Top Chicago City Tours - page 2

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

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Explore Chicago at your own pace with a 48-hour hop-on hop-off bus tour, providing unlimited access to the city's iconic neighborhoods and landmarks. Relax on open-top buses while enjoying engaging audio commentary that reveals the rich history and culture of the Windy City. This tour includes admission to the stunning 360 CHICAGO Observation Deck on the 94th floor of the John Hancock Center, offering breathtaking panoramic views of Lake Michigan and the city skyline. - Unlimited hop-on hop-off access for 48 hours across top Chicago attractions - Audio commentary in multiple languages covers local history and culture - Admission to the 360 CHICAGO Observation Deck for breathtaking views - Perfect for first-time visitors, families, and those seeking flexible exploration Time selected at booking is for 360 CHICAGO admission. Big Bus Hop-on Hop-off Tour available anytime during operating hours.

from

$33

$44

360 CHICAGO Observation Deck & Hop-on Hop-off Sightseeing Tour

(1)

Outside of Italy, few places in the world are as famous for their pizza as Chicago. Eat like a local as you travel off the beaten path to savor the city's best pizza, traveling by bus so you can cover more food hot spots in less time. Discover the science behind ingredient selection and baking as you sample slices from historic pizzerias, and take away plenty of tips to enhance your eating in Chicago.

from $84

3 hours 30 minutesFree Cancellation

from $89

On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.

Smiles ear to ear as you ride our Chicago Bike Tour through scenic Lakefront Neighborhoods. Fresh air, open paths, and lake views make this the ultimate Bicycle Tour in Chicago.

Bike Tour of Chicago's Lakefront Neighborhoods

(242)

3 hoursFree Cancellation

from $59

4.1

(55)

Chicago Helicopter 10-Minute Tour for up to Three Passengers

10 minutesFree Cancellation

from $375

Per group

Chicago Lake and River Architecture Tour

4.7

(2,317)

from $45

Immerse yourself in Chicago's thriving craft beer scene—and visit locals-loved breweries you'd be unlikely to stumble across otherwise—on this half-day brewery tour. Travel in style, and get in the spirit, aboard a traditional Prohibition–style barrel bus. Visit several unique breweries, and go on behind-the-scenes production facility tours. Discover the science behind the brewing process, and enjoy plenty of beer samples throughout the tour.

Chicago Craft Brewery Barrel Bus Tour

(347)

3 hours 45 minutesFree Cancellation

from $100

4.8

(1,638)

Chicago River 90-Minute Architecture Boat Tour

Chicago Explorer Pass: 35+ Things To Do - Includes 360 CHICAGO

from $37

3.9

(356)

1 to 30 daysFree Cancellation

from $84

4.2

(39)

Chicago Architecture River Tour & Hop-on Hop-off Sightseeing Tour

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

from $99

Chicago Walking Tour: Art Deco Skyscrapers Loop

4.8

(178)

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

from $35

Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

(905)

3 hoursFree Cancellation

from $85

Price varies by group size

Enjoy an active and entertaining way to explore Chicago’s highlights with this small-group Segway tour. Meet your guide at a convenient location in downtown Chicago, get acquainted with your Segway before setting off, and then hit the road. You’ll discover top Windy City highlights, including Millennium Park, the Buckingham Fountain, the Museum Campus, and more, all while learning about the city’s history and insider facts from your guide.

2-Hour Guided Segway Tour of Chicago

4.7

(496)

Discover many of Chicago’s best-known landmarks—and see the city dressed up in its festive best—on this holiday walking tour of the Windy City. Come bundled and join your guide and small group to explore the famous Christkindlmarket. Then continue to discover Millennium Park’s ice rink and Christmas tree, stroll the Magnificent Mile’s glowing lights, and more while you hear fun facts and cultural insights from your guide.

from $65

Glide through Millennium Park’s ice rink on your Chicago Seasonal Tour, where bright lights and winter fun capture the Chicago Holidays and Christmas spirit.

Chicago Seasonal Stroll Walking Tour of Holiday Attractions

(5)

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

from $45

Small-Group Sightseeing Boat Tour in Chicago

(95)

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.

from $89

Chicago Landmarks & Museum Campus Small Group Segway Tour

(230)

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

from $70

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

(734)

4 hours 30 minutesFree Cancellation

from $89

Have only a limited amount of time to explore the Windy City? Leave the planning to someone else with this convenient SUV transfer service. Meet your private driver at a time and place that work best for you, and set off: You’ll be dropped off directly at top Chicago landmarks like Navy Pier, Wrigley Field, Michigan Avenue, and Millennium Park, with time for solo sightseeing at each stop.

4-Hour Chicago City Tour by SUV

(2)

4 hoursFree Cancellation

from $800

Per group

Get to know the foodie Chicago neighborhood made famous by "The Bear"—and taste your way through some of the Windy City's best bites—on this small-group walking tour of River North. Visit locals-loved hotspots that represent the best of the city's dining scene, and Be sure to come hungry: You'll try everything from tacos and Italian beef sandwiches to deep-dish pizza, all while learning about the neighborhood's history and food culture.

River North Food Walking Tour

4.7

(89)

3 hoursFree Cancellation

from $89

Take your architecture spotting off the streets and inside some of the most iconic buildings in Chicago with this unique Art Deco-themed tour. Get up close and personal with the glamorous style of the early 20th century as you delve beyond the downtown facades to explore glorious interior spaces from the 1920s and 1930s, with their ornate brass and marble details, mosaics, stained glass, and other treasures that most architecture tours miss.

Chicago Architecture Walking Tour: Incredible Art Deco Interiors

(100)

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ Over 20 iconic stops ✔️ Zero wasted time ✔️ Only the best views, landmarks, and photo spots We don’t stall, we don’t drag things out — and when we say “See All of Chicago,” we mean it. From skyline views and lakeside gems to architectural icons and hidden local favorites, our guided route is packed with unforgettable stops — and none of the filler. Let’s explore the city — the right way.

from $35

Chicago City Tours See It All No Time Wasted

3.8

(20)

4 to 8 hoursFree Cancellation

from $150

Stop off the bus at Chicago Landmark Building with Prohibition Era History

4.8

(485)

Chicago Night Crimes Tour by Bus

2 hours to 2 hours 30 minutesFree Cancellation

from $55

Chicago Walking Tour: Must-See Chicago

(143)

There’s so much amazing architecture in Chicago but wandering around alone can leave you overwhelmed, and unsure of what you’re looking at. Check out some of Chicago's most important new buildings on an architecture walking tour. The tour is focused on the area around the Chicago Architecture Center (CAC), beside the Chicago River, so you don’t get overwhelmed exploring the whole city. Admission to the CAC’s galleries is also included.

from $35

Chicago Architecture Walking Tour: What's New

(82)

Chicago City Minibus Tour

from $35

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Karen_D, May 2026

Top notch!

Avery was so engaging, knowledgeable, and gave real inside into Chicago reality. Fascinating stories of the past, glorious and not so glorious. Buildings do have a life of their own and the buried stories they house are true tell alls of culture and history. Highly recommend this tour and Avery especially!

Chicago Architecture River Cruise

Carla_M, Apr 2026

Must do tour!

I did this tour last night with my husband and it was fantastic. I recommend going for the sunset option (for us this was around 6.45pm). The city architecture is stunning and our guide Sadie was phenomenal - funny, engaging and full of interesting information with a hint of dry wit! The ride was so smooth thanks to our captain and drink options were nice too. Definitely recommend! Be sure to layer up it gets real cold on the water!

Chicago Favorites Ultimate Food and Walking Tour

Lawrence_C, Apr 2026

You’re Going to Want Jessika to Feed You

Chicago Favorites Ultimate Food and Walking Tour I now know why this Food & Walking Tour is called the Ultimate. How else could one person provide you with the four uniquely Chicagoan food items in just 2 hours. Jessica was bright, fun, energetic, and knowledgeable. We tried the Chicago-style pizza, popcorn, hot dog (NO KETCHUP), beef sandwich, and got dessert too. Fun time and a full meal. This is a great food tour, walking tour, and history lesson rolled-up into one tour. Highly recommended…especially when led by Jessika.

Chicago River 90-Minute Architecture Tour

Paulina_S, Apr 2026

Quick and easy Problem Shooting

Unfortunately, traffic going there delayed us and we would have been late to our time slot. I called 30 mins in advance and they moved us to the next departing boat! Employees were professional and nice. Bobby, the tour guide was phenomenal!! Would definitely recommend.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Clarence_D, Apr 2026

Great Bday add-on

What a great birthday experience for me and my boys! The bartender, the young lady on the microphone and hospitality of all the workers was just top tier for such a nice little jam packed history listen on the water. It was my birthday and this was a great add-on to the day to add some Chicago flair to it ! 10/10

Chicago in a Day: Food, History & Architecture Walking Tour

Jaydene_H, Apr 2026

A little bit of everything in one Chicago experience

We had a fantastic time on the Chicago architecture and food walking tour with our guide, Rich. Originally from New York and now proudly calling Chicago home, Rich brought great energy, knowledge, and personality to the experience. He shared fascinating facts about Chicago’s iconic architectural design along with interesting historical tidbits. One of my favorite stops was the Tribune Tower, where Rich explained how stones and artifacts from different states and countries were donated to represent their homelands. It was such a unique and memorable detail. The food portion of the tour was equally enjoyable, featuring classic Chicago favorites like Portillo's, Al's #1 Italian Beef, and Lou Malnati's Pizzeria. My personal favorite was the Chicago hot dog—it was delicious and a true local classic. Rich also did an excellent job keeping the group on schedule, even when it was challenging to find seating in the busy fast-food restaurants. His organization and dedication helped everything run smoothly. I highly recommend this tour to anyone wanting to experience the best of Chicago’s architecture, history, and food all in one outing!

Lake Michigan Sunset Cruise in Chicago

Marla_K, Apr 2026

Bring a blanket or warm...

Bring a blanket or warm jacket. It may look like a nice day out but on the water its chilly. Bring a backpack for water or a beverage and snack. Other then that we had a great time and it was nice to see the city all lit up. So beautiful and so relaxing. If your a drinker they have a full bar. They also have some snacks. Once out on the channel you can walk about the boat. Plenty of seating.

Chicago Architecture Center River Cruise aboard First Lady

Laura_F, Apr 2026

Recommended by Chicagoan Families for Anyone to Enjoy & Gain Knowledge

This tour was recommended by both sides of our Chicagoan families when we visited because it’s the real deal. The architectural foundation not only trains the guides, but the proceeds go to support the next generation of architects. The tour did not disappoint. Our guide, Anthony was knowledgeable, funny and charismatic. Now it’s our turn to recommend this tour to family & friends.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Mohammad_R, Apr 2026

Chicago fire did us dirty..... or maybe not?!

It was awesome to visit the most dazzling architectural pieces and travel back in history to era of immediate post greater Chicago fire in 1871 when the economy was blooming and master pieces were built. Heath did a great job with leading the tour and explaining about the most interesting details and backgrounds

Chicago Night Crimes Tour by Bus

Crystal_M, Oct 2025

Had an amazing time on...

Had an amazing time on this tour!!!! Hearing the stories and stoping at some of the same locations these gangsters and outlaws actually visited , stood, worked and even lost their lives at was quite the experience! The bus driver and tour guide were very professional . Our transportation bus was very nice, clean and comfortable. So glad I took this tour!! Thank you !!!