Experience the stunning beauty of Chicago on a captivating cruise along the historic Chicago River. This architectural tour takes you down the main branch of the river, up the north branch to the East Bank Club, and then south past the iconic Willis Tower (Sears Tower) to the historic Old Post Office Building.

Marvel at the magnificent city skyline as you pass by over 40 notable buildings, including:

John Hancock Center: An iconic skyscraper that defines the Chicago skyline.

Wrigley Building: Known for its distinctive white facade and clock tower.

As you sail, an expert architecture guide will provide fascinating insights into the distinctive designs and history of these architectural marvels. Whether you're a local or visiting for the first time, this tour offers a unique perspective on one of the world's most beautiful cities.

Sit back, relax, and let the architectural wonders of Chicago unfold before your eyes. 

Chicago Architecture River Cruise 

Be inspired by the captivating, visual art that is Chicago’s legendary architecture, and the exceptional architects who created this ever-changing, dynamic legacy for all to enjoy and admire. This comprehensive 90 minute tour will navigate through the heart of the city on all three branches of the Chicago River while your professionally-trained architectural guide tells the story of more than 130 years of innovation in design, style and technique and why it is important today. The Chicago River Architecture Tour is the most authentic and encompassing Chicago experience the city has to offer. 

Chicago River 90-Minute Architecture Tour

Escape into Chicago's underworld on a crime and mob tour with stops on-and-off the luxury, climate-controlled bus. Explore historic crime scenes with great photo opportunities. Hear true crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Prohibition, John Dillinger, Frank “The Enforcer” Nitti, Cap George Streeter, Leopold & Loeb, H.H. Holmes and more. 

Visit historic landmark buildings like: The Biograph Theater, Holy Name Cathedral, Cook County Criminal Court House, Harry Caray’s Italian Steakhouse, etc. 

Tour famous Chicago neighborhoods: Streeterville, River North, Gold Coast, Lincoln Park, Old Town, Loop and Magnificent Mile. Locals and tourists agree that this educational and entertaining thing to do in Chicago is a unique cultural experience.

Chicago Crime and Mob Bus Tour 

Experience Chicago's legendary architecture and the exceptional architects who created this ever-changing legacy for all to admire. This family-friendly introduction to the Windy City's rich history and architectural heritage features highlights from Wendella's full-length architecture tours. Hop aboard our world class vessels as our local authentic tour guides showcase our amazing city. 

Chicago River 45-Minute Architecture Tour from Magnificent Mile

An authentic Chicago tradition since 1935, this is the tour that started it all. This unique excursion tells the story of more than 200 years of fascinating social, cultural and political history, and explores more than a century of groundbreaking architecture. The journey begins with an up-close perspective of Chicago's internationally-known architecture as seen from the Chicago River. Then venture through the Chicago Lock on to the calm, cool waters of Lake Michigan for expansive views of Chicago's extraordinary 26-mile skyline. Take the selfie of a lifetime on this inspirational experience! 

Chicago Lake and River Architecture Tour

Gaze upon the city sights from the pinnacle of Chicago, the Skydeck. Located on the 103rd floor of Willis Tower, formerly Sears Tower -- the third-tallest building in the world -- the Skydeck offers spectacular sweeping views and is full of interactive exhibits. To complete your exciting Chicago experience, head to the Ledge, a glass balcony showcasing unbeatable views of Chicago’s top attractions like Wrigley Field and the Navy Pier. 

We added a brand new Chicago Experience that you start with by the box office prior taking the elevator trip to the 103rd floor. It is a 45,000 sq ft. museum of today. The New Experience is part Chicago History, part Architecural tour, part Selfie Museum and part Children's Museum. This is fun and interactive for all ages. Ride our "L" Train, see our infinity pizza bed, take pictures ontop of Willis Tower and so much more! This is the best way to see Chicago in one setting. 

With mobile tickets, simply scan your phone for direct entry into the SkyDeck

Skydeck Chicago Admission Ticket

The perfect tour for first timers to Chicago or those who want to explore Chicago's famous foods along with the city's top attractions, all on one tour. Stroll the beautiful streets of downtown Chicago & taste the Windy City’s favorite eats! Bobby’s Bike Hike, whose food tours are ranked Top 10 in America (USA Today) & Top 20 in the world (Tripadvisor), offers this ultimate food & walking tour to explore the hard-working, salt-of-the earth foods Chicago made famous; a slice of deep-dish pizza, a Chicago-style hotdog, Italian beef, popcorn & brownies. Bobby’s expert guides will lead you through downtown Chicago’s most iconic landmarks; Millennium Park, State St, Chicago Theatre, Riverwalk, Michigan Ave, & the Wrigley Building, all the while explaining the tales from Chicago’s rich food-centric history. Enjoy your food tour & receive a bonus 2-hour FREE bike or kayak rental for each ticket bought, adding value to your experience. Bike along the Lakefront Trail or kayak on Lake Michigan. 

Chicago Favorites Ultimate Food and Walking Tour 

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome.

Each architecture river tour is narrated by a professional guide which leads passengers down the Chicago River to discover the city’s most renowned landmarks. In addition to historical insight on well known structures such as the Civic Opera House, Trump Tower & the Merchandise Mart, passengers will also get a chance to learn about current and upcoming developments. This Chicago River Cruise is the only cruise that navigates the three primary branches of the river including the main branch to Navy Pier, the north branch to Goose Island, and the south branch to Chinatown. It is also the cruise closest to Skydeck, has the least expensive parking, and is great for those coming from the suburbs due to its location off Interstate 290.

Chicago River 90-Minute Architecture Boat Tour

The Lake Michigan Sunset Cruise departs near the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. The Cruise will navigate from the Chicago River, through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. 

Lake Michigan Sunset Cruise in Chicago

UPDATE 2024: Don't be fooled by the copycats out there offering shady copies of our award-winning tours for $1 cheaper! There's only one company that's exclusively offered interiors-themed tours in Chicago for more than a decade, and that's INSIDE CHICAGO WALKING TOURS. Our "World Within: Dazzling Interiors of the Loop" tour is Chicago's first and best architecture interiors tour. Accept no imitations!

Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide. Ranging from stained glass mosaics from the turn of the century to soaring Art Deco spaces from the Roaring 20s, these spaces are some of the most beautiful in the city -- and open to us to explore!

Original Chicago Architecture Interiors Tour: Dazzling Interiors

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City, the 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers, including Willis (Sears) Tower. Located in the heart of downtown on Michigan Avenue, the observatory is steps away from other top Chicago attractions. It will be the high point (literally) of your Chicago trip! 

Upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. The Sip menu includes a rotating selection of beer, wine and cocktails. Once onsite, you can purchase tickets to TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. You may also choose to upgrade your Sip and View ticket from the Sip Menu to the Elevated Menu for an additional $8.



360 CHICAGO Observation Deck Admission 

Immerse yourself in Chicago's rich history and vibrant culinary scene on this captivating walking tour. Discover the city's iconic architecture and Prohibition-era charm while indulging in delectable local cuisine. From deep-dish pizza to hidden gems, savor the flavors of Chicago as a knowledgeable guide unveils the city's culinary secrets and fascinating history.

Chicago in a Day: Explore Food, History, and Iconic Architecture

Embark on an unforgettable journey along Lake Michigan and marvel at Chicago's iconic lakefront sights and attractions.

Cruise along Lake Michigan and enjoy stunning views of Chicago's renowned skyscrapers from a unique vantage point. This tour offers an amazing opportunity to admire the city's breathtaking skyline and architectural wonders. 

Sunday – Friday Cruises departing prior to 8:00pm feature recorded narration of the city’s skyline, cruises departing after 8:00pm enjoy some music and the sounds of Lake Michigan aboard our Groove Cruise.

Highlights:

Spectacular views of Chicago's famous skyscrapers

Onboard bar serving refreshing drinks

Relaxing and enjoyable sightseeing cruise

Experience Chicago like never before on this serene and scenic Lake Michigan boat tour. Remember to bring your camera to capture those social media worthy photos!

Lake Michigan Skyline Cruise in Chicago

Discover horrific instruments of torture and execution. Get a fully audio-guided immersed experience.

Explore the interactive exhibits at your own pace. Feel the chilling Ghost Hunting Experience using Ghost Hunting app. 

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city.

You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour!

Chicago Walking Food Tour With Secret Food Tours

Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running city bike tour company, on this exciting and informative adventure which recently ranked Top 20 in the World by TripAdvisor. The journey is 13 miles (at a leisurely pace) and includes deep dish pizza, a gourmet brownie, a Chicago-style hot dog, and samples of local craft beer! On the daytime version of the tour, you’ll drink in the sights of Chicago’s beautiful northside neighborhoods, including the Lakefront and Wrigleyville, home to our Chicago Cubs baseball team. On the nighttime version, you'll ride through the party districts of downtown and see the lights of Buckingham Fountain, Millennium Park and the glorious skyline. Cruise the Lakefront Trail, one of the most popular waterfront bike paths in the country. Don’t miss out on this fun tour! You’ll leave with a profound understanding of our town, even if you only came for the beer.

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. 
On this tour, you will travel through Chicago with an expert guide in a comfortable minibus, enjoy world renowned architecture including the world's first skyscrapers, Museum Campus (for the BEST skyline view in town), Millennium Park (Home of "The Bean"), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! 

You also have the option to upgrade to include THE most popular Architecture River Cruise in Chicago! For good reason, our partner Shoreline Sightseeing, has been the most booked tour on TripAdvisor for the last 5 years! And yes, there is a bar on the boat. 

The combo option will end at Shoreline Sightseeings Navy Pier location, after you finish the boat tour you will be walking distance from many other attractions in the city!

**there will be no provided transportation after your boat tour**

Chicago City Tour with Architecture River Cruise Option

The Chicago Murder Mystery Tour is an interactive history tour and game! Play detective as you unravel a murder mystery, and learn about Chicago's true crime legends and Prohibition secrets. 

This two-in-one experience combines a rich historical walking tour with an exciting award-winning murder mystery game. Perfect for people looking for a history tour of Chicago, and also for people looking for a chance to play and have fun. 

Explore a City, Solve a Murder! Only on the Chicago Murder Mystery Tour.



Chicago Murder Mystery Tour

Experience 5 must-see attractions and save up to 49% with Chicago CityPASS® tickets. One simple purchase removes the stress of planning, so you can relax and enjoy your memories in the making. With 9 days to use your tickets, you’ll have plenty of time to explore the top sights. 

Chicago CityPASS® tickets include one-time admission to 5 attractions. 

Includes: 

• Shedd Aquarium 
• Skydeck Chicago 

Plus choose 3 of the following: 

• Shoreline Sightseeing Architecture River Tour 
• Field Museum 
• 360 CHICAGO Observation Deck 
• Griffin Museum of Science and Industry 
• Art Institute of Chicago 
• Adler Planetarium 


Chicago CityPASS®

Few neighborhoods in America combine such delicious cuisine with such fascinating history as Chicago’s Chinatown. Join Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor, for an afternoon of interesting beats and scrumptious eats through Chinatown. On this 3-hour walking and food culture tour, you’ll see the bustling Chinatown Square, then get to sampling some of the richest cuisine around, including Cantonese dim sum, Portuguese-Chinese bakery treats, Szechuan style, and even Xi'an cuisine, all the while learning about the history of how these foods and cultures arrived in Chicago. This is a totally unique culinary tour experience, and not to be missed! Upon arrival to the tour, you can add a VIP Drink option for alcoholic and ethnic drink pairings! Chinatown can be challenging to navigate on your own, so let our expert guides show you the way and discover five of our all-time favorites.

Chicago's Chinatown Food and Walking Tour

Explore over 40 million artifacts, including SUE, the world’s largest, most complete T. rex ever discovered! Discover 23 mummified remains in a recreated Egyptian tomb, our dazzling Gem Hall or journey to the powerful Aztec empire! Meet Maximo our newest titanosaur at over two stories tall! The health of our guests and staff is always our top priority and we welcome you back to safely explore nearly half a million square feet of open gallery space. 

Field Museum of Natural History Admission Tickets

Enjoy Chicago’s only bus guided neighborhood pizza tour.  Eat like a local as you travel off the beaten path into Chicago neighborhoods to savor the best pizza.  Your local guide will teach you the science behind ingredient selection and baking as you sample slices from historic pizzerias.  In just a few hours, you’ll leave stuffed, and with an understanding of why pizza is such an important part of Chicago’s culture.

Chicago Pizza Tour

Our popular 90-minute daytime river and lake tour, the Urban Adventure Cruise, delights family members of all ages with incredible views of Chicago's world-renowned architecture and stunning skyline. Lively, knowledgeable tour guides bring Chicago’s rich history to life with fun stories and interesting facts. Relax and unwind on a scenic tour of the city from the unique perspective of the Chicago River and Lake Michigan. Welcome aboard!

Chicago Sightseeing River and Lake Cruise

Enjoy Chicago’s famous sights and fabulous skyline views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town) and The Buckingham Fountain. You'll also see The Magnificent Mile, Lincoln Park, The Chicago River, Millennium Park, The Gold Coast, Lake Shore Drive and more! 

Along the way, your guide will provide historical and informational and at times humorous commentary about the area and its many attractions. 
The small-group atmosphere with maximum of 13 people ensures a more personal experience. 

Chicago City Minibus Tour

Learn about the great architectural landmarks of Michigan Avenue and State Street. The 40 years between 1890 and 1930 saw the creation of some of Chicago’s the most memorable buildings, many of which are featured on this tour.

After the World's Columbian Exposition of 1893, Chicago was determined to become a great cultural and commercial metropolis. This tour is a testament to that era's ambitions. See buildings by Daniel Burnham, Louis Sullivan, Holabird and Roche and other noted architects and hear the stories behind the city's architectural gems.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: Historic Treasures of Chicago

Studio W.I.P. by Native 312 Events offers a unique spin on BYOB paint night! Join us as we host an intimate look into the world of Street Art as we learn about some different styles and techniques with guest artists. Then you get your hands dirty as you walk around our gallery setting and test out your skills in different mediums like aerosol spray and stencil. At the end of your workshop you will be able to go home with your own piece of art!

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

The Flyover experience takes 30 minutes from beginning to end. First, on-the-ground stories connect you with the spirit of the Windy City. Then, you’ll discover Chicago from a whole new perspective, as Flyover transports you over, around and through remarkable locations. You'll explore in motion with scenes captured by an award-winning creative team using custom-made drones and helicopter-mounted cameras, while scents, sounds and music deepen the immersion. It’ll take your breath away (we promise you’ll get it back). 

Flyover in Chicago

Create your own sightseeing itinerary with the Chicago Explorer Pass, saving up to 50%* off compared to buying individual attraction tickets. This multi-attraction pass, valid for 30 days after your first use, provides admission to your choice of up to seven attractions, tours or activities - all one one pass. Select from more than 25 top sites and things to do, including SkyDeck Chicago, Navy Pier and a Shoreline Architecture River Cruise. It's the easiest and most affordable way to explore the Windy City at your own pace. Simply save your pass on your mobile device (available as your 'ticket' after purchase) and go – no voucher redemption required! With Go City you can see more, do more, and save more.

*Savings based on sample itineraries on the Go City website

Chicago Explorer Pass: 25+ Things To Do - Includes Skydeck

Join us for an unforgettable afternoon on Lake Michigan with a Signature Chicago Lunch Cruise. Whether it’s a family outing or a meal with friends, upgrade your lunch with a chef-prepared buffet and sweeping views of Chicago’s iconic landmarks, such as Adler Planetarium and Navy Pier. This fun and relaxed lunch cruise experience is complete with live DJ entertainment, a fully stocked cash bar, dancing, and games on the open-air decks and indoor spaces. Set sail for a one-of-a-kind afternoon that is as scenic as it is delicious!

Chicago Signature Lunch Cruise on Lake Michigan

Enjoy Chicago’s iconic skyline with an exciting speedboat Tour on Lake Michigan. Departing from Navy Pier, the Lakefront Speedboat Tour is the best way to view Chicago from the water. Seadog offers fun for the whole family (and the dog, too!) combining an exciting speedboat ride along the shoreline with informative and amusing descriptions of the world-famous Chicago skyline!

Lake Michigan 30-Minute Speedboat Ride

There’s never been a better time to be a beer drinker — and Chicago, with its thriving brewery scene and many destination-worthy beer bars, is the perfect city for suds lovers. Visit three of its craft breweries on this all-inclusive, 3.5-4hour tour, where you’ll get to tour one brewery production facility and enjoy copious samples of local brews. To keep things interesting, you’ll travel in a barrel-shaped bus. Morning and evening departure times are both available.

Chicago Craft Brewery Barrel Bus Tour

This tour explores some of the best hidden details, secret buildings and spaces, and untold stories that add wonderful bits of color and texture to the overall narrative of Chicago. On this tour, we will explore the famous and mysterious Chicago Pedway, a system of underground tunnels connecting 40 blocks downtown, popping in and out of buildings to see beautiful and fascinating interior spaces. You'll learn to use this system that most locals don't even fully know or use, and you'll be encouraged to continue exploring Chicago on your own after the tour!

Chicago Architecture Tour: Underground Pedway and the Loop

Beat the crowds with an expert art historian guide on this exclusive early morning tour. Immerse yourself among the masterpieces housed within the acclaimed museum and listen as your guide brings each piece to life by sharing the story behind it. Let your guide lead you to the most important pieces of the 300,000-strong collection, taking the hard work out of finding where to go and what to see. Explore in a small group for a special, personal experience, and interact with your guide who can give insider’s insight into the museum. 

Skip-the-line: Art Institute of Chicago Guided Tour

Join us along the historic streets and alleys of Chicago as we walk among the spirits of mobsters and ghosts of the condemned.

This tour is for lovers of history, true crime, and haunted mysteries. Expect a sultry and gritty cocktail of Chicago's darkest stories hiding in the shadows of the Loop. From Grant Park to the Alley of Death, your expert local guide will shed light on the city’s secrets. Prepare for thrills and just the right amount of chills.



Chicago Mobs and Haunts Walking Tour

Our Chicago location is right off of the famed Michigan Ave next to countless entertainment and dining options, perfect for pairing an escape room with dinner and post-game drinks for a full night out in Chicago. Some of our fave local eateries include Big Bowl Chinese, Gordon Ramsay Burger, and Pizzeria Duo for some authentic Chicago deep dish. The best part? They're all within walking distance of our Chicago location!

The Escape Game Chicago features 5 unique themes including our cosmic adventure, Mission: Mars and our most difficult escape room, Prison Break. Every family-friendly escape game can hold up to 8 players, includes multiple rooms, and is a highly immersive experience.

These adventures offer a one-of-a-kind premium experience. Follow clues and solve puzzles to complete your mission together. We offer the best escape rooms and the fastest customer support. Come see why our escape rooms win awards.

The Escape Game Chicago: Epic 60-Minute Adventures in River North

Soak in unobstructed views of Chicago’s world-famous architecture from the water with an exciting ride on our Seadog River and Lake Architectural Tour! Start the tour at Navy Pier and sail through the Chicago Harbor Locks to the River’s iconic skyscrapers. Enjoy amusing and informative narration for a fascinating tour through the city’s architectural history as you pass the Civic Opera House, the Merchandise Mart, and the Willis Tower. Buckle up for a thrilling finale on Lake Michigan to top off this family and dog-friendly experience and cruise along the skyline at top Seadog speed!

Chicago Seadog River & Lake Architectural Tour

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour exclusive guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. 

Highlights Generally Include: (if artwork is not on loan or being restored etc.)

Paris Street, Rainy Day by Gustave Caillebotte 
Sunday on La Grande Jatte - Georges Seurat 
Sky Above Clouds - Georgia O'Keefe 
Nighthawks - Edward Hopper 
A Picture of Dorian Gray - Ivan Albright 
America Windows - Marc Chagall 
The Old Guitarist - Pablo Picasso 
Inventions of Monsters - Salvador Dali 
Four Mona Lisas - Andy Warhol 

Private Art Institute of Chicago Skip-the-Line Guided Tour 

Join this Chicago haunted pub tour which is a combination ghost tour and pub crawl that will take you on a walking tour to explore the fascinating history of Chicago and hear some of its most famous and creepy haunted stories. 

A costumed guide will lead tour goers on a 2.5-hour journey, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home. You'll visit several different bars and have time to enjoy a delicious libation (at own expense) as the guide tells them about all the spooky happenings and great history of this town!

*Tour route and drink stops are subject to availability. 
*All guests must be 21+ with Valid ID. Alcohol is not included.


Haunted Chicago Booze and Boos Ghost Walking Tour

PRICE IS PER VEHICLE AND YOU MAY BRING UP TO 5 PASSENGERS.  Thank you for contacting Chicago Private Tours! We would love to help your group discover Chicago.  Our services include pick up from your downtown Chicago hotel, a 3-4 hour private City Tour in a chauffeured vehicle, and the services of one of our knowledgeable guides. This means you will have two people working with you the entire time, allowing you to get out of the vehicle with your guide at several stops. These stops include, but are not limited to Millennium Park, Lincoln Park Conservatory, Museum Campus, and more.  The tour will be interactive and entertaining, covering history, architecture and culture.  We share stories to bring Chicago's rich history to life. Once the tour concludes, we will drop your group off at your preferred, downtown Chicago location.

Chicago Private Custom City Tour with Hotel Pick Up

Glide along the Chicago River and Lakefront as you're dazzled by the sparkle of the city at night! Enjoy breathtaking views of the dramatic skyscrapers and Buckingham Fountain's spectacular light display. Hear lively commentary as you feel the night breeze and see Chicago’s skyline transformed into a glittering jewel. A one-of-a-kind experience to scratch off your Chicago bucket list. Family-friendly cruises are our specialty!

Chicago By Night River & Lake Cruise

The Offbeat Street Art Tour is the first tour in Chicago that truly celebrates Chicago's street art scene. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene which many people overlook on a daily basis. We hope you join us to experience something truly unique in Chicago. 

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Why stress about finding a taxi at Chicago's busy airports when you can book a private car in advance? Ensure a smooth ride from Chicago O'Hare International Airport (ORD) or Midway Airport (MDW) to downtown Chicago and complete your journey in style!

Private Arrival Transfer from Chicago Airports (ORD) (MDW)

Want a quick introduction to Chicago’s magnificent architecture? This 90-minute tour takes a comprehensive look at the city’s architectural history by viewing buildings in chronological order, from early skyscrapers to new supertall high rises.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: A Walk Through Time

Immerse yourself in Chicago’s distinct skyline with bold skyscrapers and incredible views of Lake Michigan .Enjoy the efficiency of having your own local expert and personal guide to share unique and fascinating stories about the surrounding area including exclusive local insights, historic highlights and personalized recommendations. 

You and your private small group will enjoy complimentary downtown Chicago hotel pick up.

To begin your tour your Tripshepherd guide will take you to the Adler Planetarium Pier, a must-stop while in the Windy City. 

Aboard the Shoreline Architecture Cruise you will enjoy a narrated boat tour where you will see the breathtaking views of over 40 Chicago iconic landmarks, from hidden architectural features to the Windy City's most famous monuments. 

To finish your exclusive, private tour, you will get to visit two iconic Chicago landmarks - the Buckingham Fountain and the Chicago Bean (Cloud Gate).

Enjoy complimentary downtown Chicago drop off.

Best of Chicago Small-Group Tour with Architecture River Cruise

Embark on a profound, downtown walk-around, to discover incredible stories and secrets of the city on this not to miss feet on the street experience! During our loop around "Da Loop" we will peel back the layers of this Great Big Onion Town, going in and out of extraordinary buildings, admiring amazing art and architecture along the way as we uncover how it all came to be. Expect an engaging, entertaining and wide-eye-opening tour du jour of my sweet home, Chicago.

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Experience the magic of Chicago at dusk on a 90-minute live guided panoramic adventure that captures the city in its most captivating light. Watch the entire skyline come to life, from Magnificent Mile to Museum Campus and beyond. From the top deck of an open-top double decker, you’ll have a perfect vantage point to see the best of Chicago.

Witness the vibrant nightlife of River North brim with energy, trendy bars, and eclectic dining options. Your knowledgeable guide will provide fascinating insights and stories into the history and hidden stories of Chicago.

Next, the journey takes you along the legendary Michigan Avenue. From the upscale shopping and historic architecture of The Magnificent Mile to the cultural treasures of State Street Theater District, you’ll experience the diverse facets of Chicago’s most famous avenues. See renowned attractions like the Wrigley Building, Tribune Tower, and the Art Institute of Chicago, all beautifully illuminated against the evening sky.

Big Bus Chicago: Sunset Tour by Open-Top Bus with Live Guide

One actor has five shots of whiskey and then attempts to perform in a Shakespeare play. New York Times Critics' Pick!

Drunk Shakespeare Ticket – Chicago

View Art Deco masterpieces built in the heart of Chicago’s financial district during the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament.

Discover the origins of Art Deco and its hallmark motifs while admiring buildings like the Chicago Board of Trade, One LaSalle Street and the Field Building (now the Bank of America Building) -- all of which are designated Chicago landmarks.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: Art Deco Skyscrapers Loop

Segways are amazingly fun, and Chicago's lakefront, parks, and skyline are absolutely gorgeous! Add our smart, entertaining tour guides to the mix, and you have the experience of a lifetime!

Lakefront Segway Tour in Chicago

Travel on a piece of history, learning Chicago fire history as well as Architecture! We travel on Lake Michigan and through the Chicago River seeing the sights. Perfect for Fire enthusiasts, families and everyone in between! Our flagship vessel is a retired Chicago fire boat, the Fred A Busse, Engine 41, which served Chicago from 1937 to 1981. Firefighter patches from around the world and memorabilia from Engine 41's time in service, adorn the walls inside the cabin. 

Historical and Architectural Chicago Fireboat River & Lake Cruise

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2.5 hour semi-private (12 Guest Maximum) guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. 
Highlights Generally Include: (if artwork is not on loan or being restored etc.)

Paris Street, Rainy Day by Gustave Caillebotte 
Sunday on La Grande Jatte - Georges Seurat 
Sky Above Clouds - Georgia O'Keefe 
Nighthawks - Edward Hopper 
A Picture of Dorian Gray - Ivan Albright 
America Windows - Marc Chagall 
The Old Guitarist - Pablo Picasso 
Inventions of Monsters - Salvador Dali 
Four Mona Lisas - Andy Warhol 


Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

Delve deep into the world of natural history with this Field Museum All Access Pass in Chicago.  Your pass includes access to all ticketed exhibitions.  Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents. Don't forget to meet Maximo, the museum's newest titanosaur at over two stories tall!

Field Museum of Natural History All-Access Pass 

Come on our chilling ghost tour presented by US Ghost Adventures!
Book Directly With Windy City Ghosts and save $5/person.
Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets. Our Ghost Tour transports you back in time to an era of gangsters, bootleggers, bank robbers, and jazz babies. Windy City Ghosts nightly Ghost Tours take you through Lincoln Park, a beautiful North Side neighborhood with a twisted past. Learn about the forgotten burial ground that is the foundation of this bustling neighborhood. Check the bathroom mirrors in the Lion House of the Lincoln Park Zoo to make sure the ghost of a Victorian woman in white isn’t standing right behind you. Learn what spirit haunted Al Capone to the end of his days. On our Ghost Tour, you’ll hear the strange and disturbing tales associated with each of our carefully selected tour stops.

Embers of the Windy City: Chilling Chicago Ghost Tours

LEGOLAND® Discovery Center, a giant indoor LEGO world designed for families with children aged 3 to 10, is located in Schaumburg's Streets of Woodfield shopping center. The 30,000-square-foot attraction features activities ranging from hands-on LEGO play to life-sized LEGO adventures designed to provide several hours of family entertainment centered around the iconic interlocking colored bricks.

LEGOLAND Discovery Center Chicago Admission Ticket

Take a detour off the beaten path, and explore the flavors of Chicago’s vibrant West Side with Bobbys's Bike Hike, America's longest running city bike tour company, who recently ranked as Top 20 Food Tours in the World by TripAdvisor and Top 10 Food Tours in America by USA Today! This 4-hour guided food and bike tour is the perfect way to learn more about Chicago's neighboroods and taste authentic Chicago dishes along the way. You’ll explore the cultural cuisines of historic Fulton Market district, Ukrainian Village, Wicker Park, and Lincoln Park for toffee and ice cream. The tour finishes with a chocolate tasting in Old Town. You’ll learn the history of these beautiful neighborhoods and the tradition behind each of the dishes sampled. Ride through Chicago's gorgeous and unique neighborhoods, plus our legendary Lakefront Trail! There is no better way to explore Chicago than by bike!

Chicago's West Side Foodie Ride Bike Tour

Enjoy admission to more than 30 of Chicago's most popular attractions with Go City's All-Inclusive Pass. Go City lets you create your own itinerary and save far more than if you were to purchase individual attraction tickets. Take a hop-on hop-off bus tour of the Windy City, admire the stunning views from SkyDeck Chicago, and much more. You can visit as many attractions as you like over the course of 1, 2, 3 or 5 days. 

Access your Pass in the Go City App and simply simply show it at the gate or ticket office to gain admission. The App acts as your digital guidebook including attraction information and details on which attractions require reservations in advance.

Chicago Attractions Pass: Save up to 50% - Includes 360 CHICAGO

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the 20th Century Architecture of Frank Lloyd Wright List. Discover the residence Wright described as “a cornerstone of modern architecture” on guided tours that take in both the exterior and interior of the building. Inspired by the expansive landscape of the Midwest prairie, Wright’s Robie House is the most famous of the architect’s groundbreaking Prairie houses. 

Public tours are available Thursday - Monday. The museum is closed Tuesday and Wednesday. 

Save when you book directly at 
Visit to learn more.

Frank Lloyd Wright Robie House Admission

Must-See Chicago is a fast-paced, 90-minute introductory tour to Chicago featuring some of its most famous buildings, including the Wrigley Building, Tribune Tower, the Art Institute of Chicago, Willis (Sears) Tower and more!

Get a brief overview of more than a dozen buildings—as well as Chicago landmarks like Millennium Park, the Loop and the Chicago River—on this whirlwind tour. There are lots of photo opportunities along the way, so be sure to bring your camera!

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: Must-See Chicago

On this tour we visit the DuSable Museum of African American History. We visit the museum for 45 minutes. This tour visits the homes of Louis Farrakhan, the former home of Elijah Muhammad and the former home of Muhammad Ali. We will pass by the home the 44th President of the Unites States, Barack Obama as well as the home of Reverend Jessie Jackson. We provide insight on how African Americans have made a huge impact on Chicago as well as the rails, how during the Great Migration African Americans traveled to Chicago. Come tour with us!

African American Heritage Tour of Chicago 

This tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as Top 10 in America by USA Today and Top 20 in the world by Tripadvisor. Biking is easy in Chicago because of it's miles of bike trails, flat terrain and easy connections between attractions. We’ll be sampling from each of Chicago’s well known and unique foods -- deep dish pizza, a true Chicago hot dog, and a dessert for good measure. You’ll learn the history behind the foods and also get a taste for some of Chicago’s most popular downtown districts as we cruise through the Gold Coast, Chicago Riverwalk, Millennium Park, Buckingham Fountain, Museum Campus, Navy Pier and along the Lakefront. Whether day or night, you'll get fantastic views of the skyline and feel the city's vibrant energy. Veggie options available. 

Chicago Family Food and Bike Tour with Top Attractions

Tour the streets of Chicago to see the beauty and legacy left behind by the Prohibition Era. See the amazing architecture, iconic sights (both old and new), the city's best spots along the way as you explore on foot.



Explore Chicago’s Hidden Past: Prohibition Culture & Architecture

Why stress waiting for unreliable taxis or bus transfers to Chicago's busy airport? Ensure peace of mind with a private transfer from your downtown Chicago accommodation to O'Hare International Airport (ORD) or Midway Airport (MDW). Reach the airport relaxed and in good time for your flight!

Transfer services are available 24 hours a day, 7 days a week. Choose from a luxury sedan transfer for 3 people or an SUV transfer that carries up to 5 passengers. All vehicles feature stylish and spacious interiors and you will be met and escorted by a professional chauffeur.

Private Departure Transfer to Chicago Airports (ORD)(MDW)

The MCA Chicago is one of the nation’s largest multidisciplinary museums devoted to the art of our time with an international reputation for presenting ground-breaking exhibitions.

Originally conceived as a "Kunsthalle" or non-collecting art hall hosted temporary exhibitions of new and experimental artists, the museum has no permanent exhibits on view. Instead, you'll find work by living artists across media in exhibits that change every few months.

The MCA also boasts an award-winning Store and Marisol, the restaurant and bar, featuring innovative flavors in an immersive art environment. Please call the Box Office for questions or exchanges.

Chicago Museum of Contemporary Art: General Admission Ticket

Our guides present an accurate account of the activities in Chicago during the 1920's and 1930's (Prohibition Era). You will hear about the exploits of Capone, Moran, Dillinger and the rest of the boys! Some sites included are: the St. Valentine's Day Massacre, the Biograph Theater, and Holy Name Cathedral. The tour is educational but also very entertaining because our Gangster Guides are actors. Our Untouchable Tour Gangster Guides take on the persona of a gangster and have fun with it. 

Reservations are strongly recommended. 

Chicago's Original Gangster Tour by Bus

The ultimate custom sightseeing experience in Chicago! Enjoy the City from great vantage points and photograph the world-famous skyline. We zip you to many sights around the local waterways including the Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and many others. Come aboard our safe and seaworthy US NAVY built Rigid Inflatable Boat (RIB), and experience a unique & personal tour of the City!

Small-Group Sightseeing Boat Tour in Chicago

On our 3 hour food walking tour of Chicago, you will taste delectable foods from 5 different delicious places. Tease your tastebuds as you savor foods from Chicago's best deep dish pizza restaurant, Rick Bayless' amazing Mexican fare and more.  

In addition to all the delicious food, your guide will discuss the history, culture and food scene of the neighborhood. We have vegetarian options at all the food stops and can accommodate other dietary restrictions with advance notice.  

Join us on a culinary adventure of Chicago's River North neighborhood. We've done all the delicious research to showcase the best eats in Chicago. Wear your comfy shoes, bring your appetite and we'll take care of the rest...

River North Food Walking Tour

Elevate your evening with a delicious dinner and jaw-dropping panoramic views of the Navy Pier fireworks display illuminating the Chicago city skyline! On our Fireworks Signature Dinner Cruise on Lake Michigan, a dazzling show of light and color will be the backdrop to a chef-prepared buffet meal, specialty cocktails, live DJ entertainment, and dancing. From the breezy open-air decks and comfortable indoor spaces, you’ll soak in spectacular views of Chicago’s most famous landmarks, such as the Willis Tower and the Alder Planetarium. A spectacular fireworks dinner cruise on the water awaits! 

Chicago Fireworks Signature Dinner Cruise on Lake Michigan

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how it has shaped the development of buildings within the Loop.
The city's first elevated train started making trips in 1892. Now considered one of Chicago’s most defining features, the "L" offers incredible views of downtown. By being more than 20 feet off the ground, you'll see architectural details that are missed by most pedestrians at street level. This is our most comprehensive tour in the Loop, passing hundreds of buildings and highlighting ones of architectural significance. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Chicago’s most entertaining magic show! Fun, intimate, sometimes outrageous, and always hilarious.

Theater is located at 3453 N Halsted Street (near the SE corner of Cornelia Ave). Door opens 15 minutes before showtime and seating is general admission. 

Venue is BYOB for guests 21+. Cups and bottle openers are available if needed. We do not stock ice but there is a 7-Eleven just down the street (3407 N Halsted). Performance runs approximately 1 hour.

Trickery Chicago Magic Show

Chicago is home to some of the world’s earliest skyscrapers. Get an up-close look at these 19th Century marvels, learn about innovations used to build them and discover how they transformed Chicago into a center of skyscraper design and engineering.

Highlights on this walking tour include Burnham and Root’s Rookery (1888), a transitional building with a Moorish and Romanesque exterior and a stunning interior atrium re-designed by Frank Lloyd Wright; Adler and Sullivan’s Auditorium Building (1889), a masterpiece of acoustical and structural engineering; and Holabird and Roche’s Marquette Building (1895), an outstanding example of the metal frame expression with traditional details and decorations.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: Historic Skyscrapers

There’s nothing more magical than downtown Chicago during the holiday season. Bobby’s Holiday Hike is a 3hr guided walking and food tour through the Chicago Loop, brought to you by Bobby's Bike Hike, internationally recognized for their tours. You’ll get to sample the Windy City’s favorite winter treats; including a slice of deep dish pizza, Chicago-style hot dog, Italian Beef, chocolate brownie, and hot apple cider. Upon arrival, you can add a VIP holiday craft beer package for $19.99/person. Our entertaining guides will get your holiday spirit primed with plenty of food and knowledge. Did you know Rudolph the red-nosed reindeer was a story created in Chicago? You’ll see the Christmas window displays at the original Marshall Field’s department store, Chicago's city Christmas tree, the ice skating rink at Millennium Park, and the legendary Christkindlmarket, a traditional German Christmas Market. No other tour offers such an all-inclusive experience of Chicago during the holidays!

Chicago-Style Holiday Hike: Festive Food and Walking Tour

In the heart of downtown Chicago, the American Writers Museum celebrates all genres of writing through interactive exhibits and programming. From Twain to Tupac, there's a story here for everyone. Discover for yourself and visit today! 180 N. Michigan Avenue. Named Illinois' Best Attraction by USA Today and One of the 10 Best New Museums in the World by Fodor's.

Flexible Date Entry

Skip the Line: American Writers Museum Admission Ticket

Over the course of 90 minutes, explore some of the newest buildings around the Chicago Architecture Center, focusing on construction elements and their impact on the city’s built environment.

What's New looks at some of the most recent additions to the built environment surrounding the Chicago Architecture Center. This walking tour focuses on each building's height, structure, materials, ornament and its impact on the environment, the neighborhood and the city's economy. The tour showcases several recently completed buildings, including 462 N. Park and the St. Regis, and compares them to each other in order to observe emerging patterns. These new additions are also contrasted with some of the older buildings downtown as a way to highlight developments.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Architecture Walking Tour: What's New

When you arrive at the Chicago Lincoln Park indoor skydiving location, get started by putting on your provided gear and going through a specialized training session from a flight instructor.

Learn how to safely float in a 1,400-horsepower vertical wind tunnel that generates a wall-to-wall cushion of air, commonly used by professional skydivers. Experience the thrill of skydiving without having to hurl yourself from an airplane, and no experience is necessary.

Once inside the enclosed space of the flight chamber, a tunnel operator slowly increases the wind speed until you and your instructor are airborne. Feel your adrenaline pumping as you 'free fall' at wind speeds reaching 180 mph (290 kph). The stable wind flow keeps you from falling off the column of air, and your instructor is on hand at all times to guide you. The first-time flyer experience takes about 75min. Each session includes up to 12 people, but fly one-on-one with your instructor in the wind tunnel twice for 60 seconds.

Chicago Lincoln Park Indoor Skydiving with Two Flights

A breathtaking evening of elevated dining and spectacular fireworks views awaits on our Fireworks Premier Dinner Cruise on Lake Michigan! There’s no better way to marvel at Navy Pier’s dazzling fireworks display than from an unobstructed vantage point on the water. This upscale evening features a chef-prepared plated meal, craft cocktails, and exceptional service. You’ll soak in sweeping views of the glittering city skyline from the open-air decks and comfortable indoor spaces while our live DJ plays all your favorite hits. Delight in a truly memorable dining experience on the water!

Chicago Fireworks Premier Dinner Cruise on Lake Michigan

Experience the story of Chicago through its skyline on a walking tour that stretches from the city’s 19th-century roots to its most striking modern towers. From Beaux-Arts to modernist to Art Deco, this architecture tour has it all.

Start near beautiful Millennium Park to enjoy those lakefront views. Then follow your guide past architectural gems from the 1920s and landmarks like the Wrigley Building and Tribune Tower, plus eye-catching storefronts including the world’s largest Starbucks and a Harry Potter-themed shop. 

Step off Michigan Avenue to explore luxury spots like Cartier and St. Laurent before wrapping up at the former John Hancock Center. If you’ve selected the upgrade, you’ll head up 1,030 feet to 360 Chicago to be dazzled by panoramic views of Lake Michigan and the pinnacles of skyscrapers below your feet. 

Come see what makes this mile truly magnificent!

Magnificent Mile Tour With Optional 360 Chicago Upgrade

Enjoy a private two-hour sailing experience for up to six people along Chicago’s beautiful lakefront. Kick back, relax, and let the US Coast Guard licensed captain treat you to stunning views of Chicago’s spectacular skyline. Make the experience your own. The flexibility of a private charter allows customization of virtually any aspect of the sailing adventure from guest list to music selection to sailing route. Three departure times offered daily. This experience is not meant to be an in-depth guided tour; however, our captain is always happy to point out interesting sights with anecdotes and historical information. Just ask you captain. Looking for a sunset sail, see our other product listing "Come Sailing with us at Navy Pier - Sunset Sail on Lake Michigan". Looking to watch the Navy Pier Fireworks from a private sailing charter, see our other product listing "Come Sailing with us at Navy Pier - Saturday Fireworks Sail". All charters are NON-SMOKING experiences.

Private Sailing on Beautiful Lake Michigan - Navy Pier, Chicago

Let our expert local guides share their passion with you for The Art Institute of Chicago on this private 2 hour tour. As you traverse the hallowed halls, you’ll discover an extraordinary collection spanning centuries and cultures, from classical masterpieces to cutting-edge contemporary works. Our expert guides will illuminate the stories behind each brushstroke, sculpture, and masterpiece, providing a rich narrative that breathes life into the art.

Art Institute of Chicago Private Expert Guided Tour

The Chicago Architecture Center (CAC) was founded in 1966 as the Chicago Architecture Foundation to save the historic Glessner House. Since then, the CAC has grown to become one of the largest cultural organizations in Chicago. Visit the CAC to view our 4,250-building scale model of Chicago, shop in our award-winning store or participate in a fun family event in our ArcelorMittal Design Studio. 

On the Chicago Model, view more than 4,200 buildings in one spectacular room at the cinematic and interactive Chicago City Model Experience.

At the Chicago Gallery learn how Chicago became the "city of architecture," with a look at its fascinating neighborhoods, housing styles and famous architects.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Architecture Center Exhibits Admission

360 CHICAGO Observation Deck sits 1,000 feet over Chicago’s legendary Michigan Avenue. Located on the 94th floor of 875 N. Michigan (formerly the John Hancock Center), 360 CHICAGO gives you the opportunity to experience what 'Travel & Leisure Magazine' voted one of the best views in America.

360 CHICAGO’s concourse level includes an interactive exhibit highlighting the history of Chicago and the vibrant cultures and businesses across Chicago neighborhoods. Explore Chicago beyond downtown after watching a short documentary titled 3 of 77 featuring an immersive view of three Chicago neighborhoods. 

While taking in the views enjoy a beverage from the newly renovated CloudBar. Serving up iconic Chicago snacks, like Garrett’s popcorn, and neighborhood-inspired cocktails with local brewery, Moody Tongue on tap. Guests receive one beverage from the Sip Menu with their ticket.

*TILT not included in the purchase of your general admission ticket. MUST UPGRADE ON SITE.


360 Chicago Observation Deck Sip and View Ticket

Get the best of both worlds: explore Chicago’s stunning architecture while uncovering its dark past. Inspired by Devil in the White City, this expert-led walking tour reveals the secrets of the city’s skyline and its shadowy history. Led by a passionate local guide, you’ll visit architectural gems and hidden landmarks that boat tours miss bringing Chicago’s rich and eerie past to life.

Chicago Architecture and True Crime History Tour 

Though the Art Deco style throws us back in time, it’s actually a futuristic style — it’s meant to make people in the 1920s think of the future. The gleaming materials, the perfect precision of the details… it’s the epitome of glitz, glam, and elegance. On this tour, you’ll walk in the footsteps of those high on the potential of the future, before the infamous Crash of ‘29. We’ll explore several stunning interior spaces within the Loop and near the Chicago River, going inside not only the great Art Deco buildings of the Loop, but also a few buildings you’ll recognize from popular boat tours. But the great thing is that you’ll go where most boat tour guests won’t ever go: inside these gorgeous Art Deco buildings, where you’ll be amazed by the beauty that people don’t know is right there behind closed doors.

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

Tour the lobbies of five opulent Art Deco skyscrapers built near the banks of the Chicago River during the business boom of the Roaring '20s. Learn how Art Deco reflected the era’s fun-loving optimism with lavish materials and geometric ornament. Discover the origins of Art Deco while admiring buildings like the Carbide and Carbon Building (now Pendry Chicago), the Chicago Motor Club Building (now the Hampton Inn) and the colorful, but often overlooked, Trustees System Service Building (now the Century Tower)—all of which are designated Chicago landmarks. As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

On our Secret Food Tour: Chicago, you'll enjoy a variety of foods with culinary influences from the people who built this city.

You'll experience all the city's biggest food hits, many dishes with roots dating back over 150 years. This moving feast incorporates a walk through some of the city's world renowned architecture and public art in the famed Chicago Loop District. Experience our famous deep dish pizza, taste the amazing Italian beef sandwich, enjoy gourmet popcorn, and lots of other treats. Plus, there is our mouth-watering secret dish that you can only find out about on the day of the tour!

As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!

Chicago Private Walking Food Tour With Secret Food Tours

Looking for iconic Mid-Century Modern architecture? What better place than Chicago with its triumvirate of modern architects (Mies van der Rohe, Bertrand Goldberg and SOM) and a city ready and willing to accept them. Find out what set these buildings apart from their predecessors and how they helped set the stage for the future.

If you’re interested in iconic buildings, public art, urban planning or government this is your tour. Find out the stories behind inland steel, Marina city, the IBM building and other "Mad Men" worthy skyscrapers.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: Modern Architecture

Explore Chicago at your own pace on an independent bike tour. With your full-day bike rental, pedal along Lake Michigan and visit top Chicago attractions such as Lincoln Park, Navy Pier, Millennium Park, Wrigley Field and the Shedd Aquarium. This is a fun and active way to experience the city with the whole family, and you can enjoy the flexibility to create your own itinerary with the help of your provided map.

Chicago Full Day Bike Rental

Located just outside of Chicago, the Volo Auto Museum features over 33 exhibits and display attractions. The museum was built on a farm from the 1800's and features many of the original buildings along with their country charm and character.

Volo Auto Museum: Admission Ticket

This tour will show you many of these delightful cottages and the different styles they were designed and constructed in. You will also learn about their history and unique part of the growth of the city of Chicago. Plus you will hear about other fascinating Chicago history that dates back 150 years and beyond! The Oldtown Triangle is one of the oldest and most quaint areas of the city - an area that many Chicagoans love and cherish. You will feel like you have left the hustle and bustle of the city and will instantly be transported to another place, another time, specifically the late 1800's!



Workers Cottages of Oldtown Triangle Walking Tour

No visit to Navy Pier is complete without a ride on the Centennial Wheel, Navy Pier's iconic, 200-foot-tall Ferris wheel, promising unparalleled views of Lake Michigan and the Chicago skyline. Each gondola seats up to 8 guests and is fully enclosed for year-round comfort.

Chicago's Navy Pier Centennial Wheel Ticket

This unique tour of Chicago will allow for tourist to see most of Chicago’s 77 neighborhoods and city parks. There is no other tour that tours multiple neighborhoods in Chicago. Some tours show 1 or 2 neighborhoods, we travel through the South Side, North Side, Southwest, Northwest and a portion of Downtown showing more then 10 neighborhoods and attractions. 


Small-Group Tour of Chicago Neighborhoods: North and South Side

From mysterious sightings creepy haunts, mobsters and more, you'll hear stories of Chicago's darker side on our newest nighttime tour. Cruise the Chicago River amidst twilight tales of the city you never knew existed... and might wish you could forget.

Not to mention the nighttime views of the lit-up architecture in the heart of Chicago!

Please arrive 30 minutes in advanced!

Chicago Creepy Cruise

Learn about the life and work of Louis Comfort Tiffany as we visit some of Chicago’s most magnificent art-glass and mosaic installations, each designed and crafted by the Tiffany Glass and Decorating Company.

In the late 19th Century, the Arts and Crafts movement revived an interest in decorative glass. New, well-regarded homes and public buildings from the era were considered incomplete without decorative glass or mosaics. Louis Comfort Tiffany, the preeminent practitioner of this art, gained great exposure for a chapel he designed for the 1893 World's Columbian Exposition in Chicago. Today, the city is home to one of the largest collections of Tiffany art glass in the United States. This tour introduces some remarkable examples of Tiffany's work.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: Tiffany Treasures

Get an exclusive behind-the-scenes look at the hit NBC drama Chicago Fire TV Show Set Tour. Visit the actual filming locations where the show comes to life. 

Tour Highlights:
- Explore the iconic Firehouse 51 exterior
- Visit the Molly's Bar a fictional bar on the show, but a real pub in Chicago.
- Visit the famous Bean (Cloud Gate) at Millennium Park 
- Visit the Chicago Cultural Center renowned for its stunning architecture, including the world's largest Tiffany stained-glass dome.

This tour is subject to filming schedules, and it can be customized to your needs. Tour participants are respectfully advised that this is an active firehouse; please be mindful of operations and follow guidelines, noting that the tour is independently operated and separate from the fire department.

Additionally, For visits to Firehouse 51, the Bean, and the Chicago Cultural Center, please note that the tour guide will not accompany visitors, but detailed instructions will be provided.

Private Chicago Fire TV Show Set Tour

Chicago is the birthplace of the skyscraper: imagine what incredible stories of engineering feats it has to tell!

Join Inside Chicago Walking Tours on our newest route — it’s Chicago’s ONLY engineering-themed tour! You’ll cover more than 150 years of engineering evolution, learning from a real engineer who makes the information accessible and graspable without ever dumbing it down. We believe that everyone can understand and be fascinated by these concepts if taught in an engaging and fun way.

You’ll see a building from the “father of the skyscraper,” who was actually an engineer and a classmate of Gustav Eiffel. You’ll learn how a “haunted” building gets its reputation simply by settling unevenly on its “floating” foundation. You’ll marvel at how Chicago’s buildings handle gravity and wind. 

And as on all of our tours, you’ll visit the interiors of a few buildings to truly get that sense that you’ve seen inside Chicago!

Marvels & Feats: An Engineer's Tour of Chicago Architecture

Indulge in a VIP dinner experience at Chicago’s Skydeck, offering breathtaking views from 1,353 feet (412 meters) above the city. Located in the iconic Willis Tower, this exclusive experience lets you enjoy the stunning skyline after hours, once the Skydeck is closed to the public. Savor a delicious meal featuring your choice of Chicago’s famous deep-dish pizza, a fresh salad, dessert, and refreshing non-alcoholic beverages. Perfect for a special occasion, this unforgettable evening offers both locals and visitors a chance to dine with a view like no other. Book your VIP dinner now for an extraordinary experience high above the city!



Skydeck Chicago Pie in the Sky Dining Experience

Taste fresh baked goods, Chicago Deep Dish, 'snappy' Chicago Hot Dogs, and more as you unravel a mystery! 

The Chicago Murder Mystery Food Tour is an interactive and tasty experience that combines history, game-play, and a deliciously planned meal with murder!

This is the adventure that you and your friends and family will talk about from your trip to Chicago. Give the experience they'll remember, only on the Chicago Murder Mystery Food Tour.

Solve a Murder on a Chicago Food Tour with Fun Guide

Much of the historical information shared on this tour is unknown to most attendees. This tour also shows everything from the gritty to the pretty, from the mundane to the magnificent.

Historic Homes and Cottages of Wicker Park Walking Tour

Looking for a unique Chicago tour? Glide into the city’s dark past with our unique Segway tour, where ghosts, gangsters, and true crime come to life.

Cruise to eerie sites like the Iroquois Theater Fire, one of the deadliest disasters in U.S. history. Ride past Marshall Field’s, where ghostly sightings have been reported..

No gangster tour is complete without The Outfit’s underworld. Roll past mob-run speakeasies & the site of Antonio Lombardo’s brutal assassination. Hear chilling tales of Capone’s rule, secret tunnels, and crime scenes that shaped Chicago.

This spine-tingling tour is perfect for ghost hunters, gangster buffs, and true crime fans.

Tour Highlights:
Visit haunted sites like the Iroquois Theater Fire & Marshall Field’s
Hear eerie ghost stories from Chicago’s most famous haunted locations
Learn about Al Capone, The Outfit, and Chicago’s most infamous gangsters

Book Now to explore Chicago’s haunted history and gangster legends on this thrilling Segway adventure!

Chicago Segway Tour: Haunted Crime & The Outfit

Discover how a dirt road known as Pine Street transformed into a "Paris on the Prairie" and later into the Magnificent Mile, the city’s premier shopping district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons.

Developed over the past 100 years, the street includes historically-inspired architecture in Parisian, Gothic, neoclassical and Art Deco styles sprinkled among Modern and 21st Century buildings. You’ll see skyscrapers, vertical malls, hotels, residential towers and some buildings that were designed to embody the brands sold inside.

As a certified nonprofit, all CAC ticket purchases directly support our education efforts and community engagement projects.

Chicago Walking Tour: The Magnificent Mile

Skip the stress of a taxi or shared shuttle between Chicago downtown and O'Hare  airports with the Highest rated limousine service in Chicago on Trip Advisor and Yelp. A professional driver will pick you up at Chicago O'Hare Airport at curbside. Travel in a comfortable, newer private sedan for a safe and relaxed ride. All our drivers are licensed and insured and all our sedans carry a $350,000 insurance policy. Ensure a hassle-free arrival at Chicago O'Hare International Airport (ORD) with this private transfer service to your downtown Chicago hotel.


Experiences in Chicago, United States