All Chicago Tours &amp; Excursions in 2026

Chicago Walking Tour: Tiffany Treasures

Experience Chicago in a new way on this small-group Segway tour. Visit Chicago’s "front yard," and see more of the sights in less time. Glide along the fragrant floral paths of Grant Park to the famous Buckingham Fountain. Then, travel along the banks of Lake Michigan to the Museum Campus for top-notch views of the city’s iconic skyline. Guided Segway training and helmets are included, making this a beginner-friendly tour.

Chicago Landmarks and Museum Campus Small Group Segway Tour

Explore Chicago like a local—and visit the city’s distinctive, characterful neighborhoods, in addition to its major landmarks—on this Half-day tour. Set off from downtown with just a small group for company, and leave the driving to your guide—you’ll explore dozens of Windy City neighborhoods, from Hyde Park and Bronze Ville to Lincoln Park and the Gold Coast. Learn all about Chicago culture and history as you go.

Small Group Tour of Chicago Neighborhoods: North and South Side

4 hours 30 minutesFree Cancellation

Immerse yourself in American literary traditions, and enjoy a wide range of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 2017, and is one of the city’s newest highlight institutions. Guarantee your admission, and prevent any travel hassles, by securing your tickets in advance. Once inside, you’ll have time to explore at your own pace.

American Writers Museum Admission Ticket

1 to 5 hoursFree Cancellation

Chicago P.D. TV Show Set Tour

Chicago Riverwalk Self-Guided Walking Tour

Special Offer

1 to 2 hoursFree Cancellation

Discover Pilsen, one of Chicago’s most vibrant neighborhoods, known for its colorful street art, rich Mexican heritage, historic architecture, and thriving local culture. This locally led Pilsen walking tour offers an authentic, insider experience beyond typical Chicago sightseeing. - Pilsen-based experts with 40+ years of combined experience - Explore iconic sites like 16th Street murals, Thalia Hall, and local cultural landmarks - Official Pilsen tour partner of the Chicago History Museum - Bilingual tours available in English and Spanish - Multiple routes and flexible options, including walking, running, or biking tours -BOOKING: Please note the tour guide will contact you to schedule an exact time for your tour after you have completed the booking. There is no option to pick a start time.

Pilsen Chicago Walking Tour: Street Art & Mexican History

1 hour 15 minutesFree Cancellation

Candle Making Experience Near Museums & Millennium Park

Discover the amazing history and architecture of Chicago with expert tour guide Dave Lineal. Walk among gigantic towers of downtown and learn how Chicago became a global force in culture, commerce, and architecture. Our tour will explore building interiors like the world's oldest skyscrapers, City Hall, the underground Pedway, and the old library. We will observe public art like the Picasso and the Bean. While immersed in the places where it happened, Chicago's colorful stories will vividly spring to life. This walking tour aims to enhance your understanding of modern-day Chicago by a deep dive exploration of its history. Your guide to the city is the friendly and well-informed Dave Lineal: local artist, culture vulture, and historian. Dave is tested and certified by the Chicago Tour-Guide Professionals Association. This is an outdoors / indoors all-weather walking tour with a duration of two hours. We will meet under the marquee at the Chicago Theater, 175 N. State Street.

History and Architecture of Chicago Loop Walking Tour

To me, one can appreciate a given building, or piece of public sculpture, far better when a tour guide explains the historical and cultural context. What was important in that era, and what was the architecture of that era thus trying express? I do know a lot about this. Thus, you will gain this information about each point of interest. I have taken other tours here, and I just do not hear a word from that point of view. This tour will be like an open history book to an America that no longer exists: Roman and Greek architectural styles, as well as French and British-influenced styles. Of course, you will see the latest in office building architectural styles from around the world, for those of you who just love the modern era as well.

Architectural and Historical Private Tour in Downtown Chicago

2 hours 20 minutes to 2 hours 30 minutesFree Cancellation

Forget the history you learned in school—Chicago’s story looks very different when told through the women who helped shape it. On this captivating 2-hour walking tour, discover trailblazers like Ida B. Wells, Jane Addams, Katherine Buckingham, and Jeanne Gang while exploring some of Chicago’s most spectacular and often overlooked architectural interiors. Step beyond the famous landmarks to uncover women who challenged convention, created groundbreaking art and architecture, fought for justice, and helped shape the city we know today. Your expert local guide brings their stories to life, revealing fascinating details most visitors—and even locals—never hear. - Discover the untold stories of extraordinary Chicago women - Step inside beautiful, hidden architectural interiors - See Chicago history from a fresh, empowering perspective - Support a local, woman-owned small business Starts near Roosevelt University and ends in Millennium Park.

A Woman's Place: The Chicago Women's History Walking Tour

Step into Chicago’s coolest hidden bars on a mid-century cocktail adventure! Join a local guide to discover vintage lounges, secret speakeasies, and retro bars most tourists miss. Savor expertly crafted cocktails (own expense), hear untold stories of the city’s nightlife boom, and soak in stylish decor straight from the 1950s and 60s. This small-group tour is perfect for cocktail lovers, architecture buffs, and anyone seeking an off-the-beaten-path night out in the Windy City.

Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

Our tour will take you through Millennium Park, starting at the Millennium Park Welcome Center. We’ll wander past shining sculptures, playful fountains, and peaceful gardens, all while soaking in the city’s energy, ending at Queen’s Landing, where the city meets the lake, and the skyline stretches as far as you can see. You'll learn the history of the city, see the sites, learn about what you are seeing and be guided step by step by our walking tour app.

Chicago’s Millennium Park Self Guided Audio GPS Walking Tour

1 hour to 1 hour 30 minutesFree Cancellation

5% savings

from

$10$9

Illinois Holocaust Museum Experience360 Admission

1 to 2 hoursFree Cancellation

We'll explore five (5) of our favorite, Handcrafted Local Micro Breweries in two special locations of the historic, Chicago landmark district, Fulton Market; which used to be the meatpacking district, now becoming the Chicago Brewery District. Here you'll experience the fabulous, intricate world of the art of beer creation. We will all meet at the first one, introduce ourselves and try some delicious appetizers; where Carla will make a special Homemade Guacamole and Homemade Tortilla chips, and here, the first 3 handcrafted beers (3-5oz beers) are on us. Then we'll walk to the other breweries where you'll have a chance to order other beers and serve your own. Here you can stay as long as you want after the tour. During our expedition, we can all share our opinion about the flavors, the creation, etc... All the breweries are within walking distance.

Chicago Local Brewery Expedition with Homemade Guacamole

Price varies by group size

Every Friday & Saturday at 10:30pm, Sundays at 7:00 at The Neo-Futurist Theater, the Neo-Futurist Ensemble attempts to perform 30 original, handcrafted, radically honest plays in the ever-shrinking span of 60 minutes. Each play offers something different, be it funny, profound, elegant, disgusting, topical, irreverent, terrifying, or musical; all are ORIGINAL, truthful and tackle the here-and-now, inspired by the lived experiences of the performers. With new plays every week, THE INFINITE WRENCH is The Neo-Futurists’ ongoing and ever-changing attempt to shift the conventions of live performance and speak to those unreached or unmoved by traditional theater. Masking is optional on Friday and Saturdays. Masks are required on Sundays.

The Infinite Wrench: Experimental theater in Chicago

The Infinite Wrench: Experimental theater in Chicago

1 hour 20 minutesFree Cancellation

Chicago All Day Water Taxi

20 minutesFree Cancellation

Considered Chicago’s original “Millionaire’s Row,” Prairie Avenue in the Near South Side is renowned for its Gilded Age mansions—and this tour makes exploring easy (and delightfully spooky). In the evening, meet your guide in front of the Glessner House, and set off with ghost-hunting gear to accompany you. In between spotting highlights including the Marshall Field Jr. Mansion and the Henry B. Clarke House, you’ll hunt for specters and hear ghost stories.

Prairie Avenue Haunted History Tour and Ghost Hunt

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at your own pace and schedule -Professionally produced, narrated and musically edited immersive experience -Guided by technology. Put your phone in your pocket as the smart phone tour guided you with voice turn by turn. -Great deal -See and learn about Chicago's haunted spots, tragic events, fires, and the spirits that stayed behind. -Listen again after taking the tour. -The tour never expires, go or listen (after the on location tour) anytime. This haunted adventure is a smart phone guided on location tour. You go to the first stop, open the tour, enter your experience code and press play. From there you are guided turn by turn through Huntsville. The app knows your location and seamlessly guides you each step of the way.

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

1 hour to 1 hour 15 minutesFree Cancellation

Learn the secrets of making one of Mexico’s most celebrated dishes during this beginner-friendly, local-hosted cooking class. Meet your Michelin-trained chef guide at her home, enjoy a refreshing hibiscus agua fresca upon arrival, and roll up your sleeves. Your guide will break down the steps to make an authentic mole sauce, and share tips as you go. Finally, sit down to enjoy your tasty and traditional meal.

Learn To Make Mole The Real Mexican Way Before Lunch

PRIVATE Online Chicago-Style Deep Dish Pizza Class with Nancy

Price varies by group size

5.0

(4)

from $59

LEGOLAND Discovery Center Chicago Admission Ticket

Bring the kids to LEGOLAND® Discovery Center in Schaumburg for a day of brick-building adventure. With 30,000-square-feet of space this family-friendly attraction has activities for everyone: from an interactive pirate-themed playland to a factory tour where you can actually see how LEGO bricks are made. There's even a mini replica of famous Chi-town landmarks made from nearly 2-million LEGO pieces.

LEGOLAND Discovery Center Chicago Admission Ticket

3 hoursFree Cancellation

3.0

(117)

from $23

Chicago is renowned for its wealth of spectacular architecture—and this small-group tour gives you the special chance to discover building interiors that most visitors overlook. In the afternoon, meet your guide in Downtown Chicago, and get ready to discover the interiors of five of the city’s most striking art deco skyscrapers. As you go, soak up the skyline views, and learn more about the city’s unique architectural history.

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

Chicago Walking Tour: Art Deco Skyscrapers Riverfront

Discover Chicago's iconic sights on this guided walking tour that highlights five scenic photo spots. With a local guide, enjoy stunning skyline views and learn fascinating stories about the city’s history and culture. At each stop, professional photos will be taken of you or your group, allowing you to take home original digital images that capture your adventure in the Windy City. - Visit five picturesque locations for memorable photos - Enjoy breathtaking skyline views throughout the tour - Receive original digital photos after the tour to keep the memories alive - Perfect for couples, families, or anyone wanting to explore Chicago through photography

Chicago Photo Capture Your Adventure Walking Tour

2 hours 30 minutesFree Cancellation

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago By Night River and Lake Cruise

Gloria_S, Oct 2026

Beautiful sunset boat ride

This night boat ride was amazing! We took the 6:30 boat, and seeing Chicago at night, and the shoreline was magical. The boat went down the river slowly with narration the whole time. Matthew was very knowledgeable, and we leaned many things we never knew about the history of Chicago. We also went through the locks out to the lake, and had a smooth ride along the shoreline, and Matthew pointed out different buildings along the way! Bring a warm coat or blanket if it's cool out- and enjoy the ride! We would definitely recommend this !

Chicago River 90 Minute Architecture Tour

Dennis_G, Oct 2026

Great day on Chicago Architectural Boat Tour

Great tour. Not only learned about Chicago architecture, but also about the history of Chicago. Our tour guide, Spiro, did an excellent job of combining architecture, history, with enough humor to keep it all interesting. To top it off we had a beautiful fall day.

Flyover in Chicago

Sandra_B, Oct 2026

Fly Over Chicago.

⭐⭐⭐⭐⭐ An Incredible Experience! Flyover Chicago was absolutely amazing! From beginning to end, it was such a fun and exhilarating experience. The breathtaking scenery, incredible visuals, and sensation of soaring through the air made it feel like I was actually flying. Whether you’re visiting Chicago or live in the area, this is an attraction you shouldn’t miss. I would absolutely do it again. I only wish it lasted a little longer.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Cheryl_E, Oct 2026

It was evening and...

It was evening and drizzly/rainy. The buildings could not always be seen as they drifted in and out of clouds (magical and mysterious). The tour guide also shared lots of fun trivia and history. It was my two teen children's favorite Chicago experience. Highly recommend!

Chicago Architecture Center River Cruise aboard First Lady

Fran_S, Oct 2026

Best activity once you arrive in downtown Chicago!

I’ve taken this tour two times this year while entertaining family and coworkers from our of town and they absolutely love the tour. The tour operators are so well educated and do such a wonderful job at moderating and really showcasing Just how beautiful Chicago is for all its architecture and would recommend this to anybody visiting the city!

Chicago Sightseeing River and Lake Cruise

Nahrain_C, Oct 2026

Beautiful Chicago Experience

The boat guided was wonderful. The narration of Chicago's architectural history was interesting and informative. Everyone on board was friendly and accommodating. My only drawback was that it was not handicap accessible (not that I saw, anyway). Taking 2 flights of stairs down and then up again afterward is not easy for seniors or people with leg injuries/medical issues.

Chicago Architecture River Cruise

Rachel_G, Oct 2026

Cool experience and take your dogs if you can!

This was a really cool experience and a great way to see the Chicago River and the Chicago skyline. The history was interesting and Mac our guide was great and super informative. We traveled with our 2 dogs and the boat was gentle enough that you barely felt like you were moving. Money well spent!

Chicago River 90-Minute Architecture Boat Tour

Sharolyn_B, Oct 2026

The dock is a bit run...

The dock is a bit run down. There are at least porta-potties. The seating on top of the boat is folding chairs, but pretty comfy ones. But the tour guide was just amazing! So knowledgeable, and he gave a really good mix of historical facts, interesting happenings, Chicago culture, and humor. Very enjoyable!

Chicago Crime and Mob Bus Tour

Leslie_P, Sept 2026

It would be a crime to miss this tour!

I have taken several Viator tours, and they NEVER disappoint! The Mob and Crime Tour was no exception! Jay possesses an impressive knowledge on the subject, and the presentation was balanced to provide people with limited knowledge of Chicago history a good foundation in the subject, yet offered plenty of specific, anecdotal, and trivial facts to further inform and educate guests familiar with "the players" and events of crime in Chicago. The pacing of the presentation was excellent, and information was delivered in an entertaining and interesting way. Jay was quite skillful at adjusting the presentation to coincide with sites as the bus was driving by. I appreciated the fact that participants were able to leave the bus at the Biograph Theater to spend a little time rather than just driving by. That was a highlight of the tour! All of my other Viable tours have been walking tours -- this was my first bus tour. The bus was clean and comfortable and the driver did a great job navigating traffic -- way to go, Tommy! Jay & Tommy make a great team, and did their very best to make the tour fun & informative. Thanks to both of you for a great tour! I highly recommend this tour --you won't be sorry!

Chicago Lake and River Architecture Tour

Tamara_P, Sept 2026

This was a perfect ...

This was a perfect activity for anyone who loves to see the history of Chicago and experience the beauty of the outdoors on the river and lake., we loved it , the tour guide was not only knowledgeable but funny as well ! We enjoyed it and would recommend anyone to do this trip it was about and 1 1/2 hours which was the perfect amount of time .highly recommend!