Top Chicago City Tours

Chicago River 90-Minute Architecture Tour

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

(10,046)

from $45

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

3.9

(2,253)

from $49

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

(16,139)

from $39

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Join us in the daytime or evening for City lights and breathtaking views

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

(3,216)

from $28

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Chicago City Minibus Tour

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

(577)

from $50

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Explore the Loop’s civic, financial, and architectural core, admire world-renowned towers, and experience Chicago’s most celebrated public spaces. This small-group tour offers a comprehensive introduction to Chicago’s skyline, history, and urban design, concluding with a panoramic skyline view before returning guests to the original pickup point. Ideal for first-time visitors and architecture enthusiasts alike. Explore Chicago’s iconic riverfront skyscrapers and historic bridges See legendary architecture including Willis Tower and Marina City Discover the heart of Chicago’s financial, civic, and architectural power Pass by Millennium Park and spend time at Cloud Gate (The Bean) Enjoy a panoramic Chicago skyline view, included for all guests

(2,095)

from $85

Special Offer

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

Premium Chicago City Tour Small Group ICONIC Landmarks & Skyline

3 hoursFree Cancellation

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

Lake Michigan Sunset Cruise in Chicago

Chicago Crime and Mob Bus Tour

4.5

(1,553)

from $45

Special Offer

1 hour 30 minutes to 2 hoursFree Cancellation

Chicago Lake and River Architecture Tour

Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

(2,338)

from $45

A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.

Chicago's Chinatown Food and Walking Tour

3 hoursFree Cancellation

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

(678)

from $80

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Chicago City Private Tours

5.0

(1,636)

from $35

2 to 8 hoursFree Cancellation

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

(28)

from $199

Per group

Total Chicago: From Architecture to Food

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

4 hours 30 minutesFree Cancellation

Price varies by group size

(1,238)

from $101

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Chicago City Tour with Architecture River Cruise Option

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

(720)

from $50

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

3 hours 45 minutesFree Cancellation

(348)

from $100

Experience Chicago in Style with Our Luxury City Sightseeing Minibus Tour. Indulge in the ultimate Chicago adventure on our top-rated, luxury sightseeing minibus tour. This 2-hour, expertly guided experience takes you through the vibrant heart of the city in a sleek, climate-controlled minibus designed for comfort and class. Marvel at iconic skyline views and the shimmering waters of Lake Michigan from panoramic windows, and enjoy curated photo stops at the city's most breathtaking landmarks. With engaging stories from your private guide and an intimate, upscale atmosphere, this tour offers an unmatched blend of elegance and exploration. Please note, infants 0-3 years old must sit on a lap.

Luxury Minibus Chicago City Tour

Chicago Sunset Tour by Open-Top Bus with Live Guide

(6)

from $65

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.

4.1

(171)

from $48

2-Hour Guided Segway Tour of Chicago

(497)

from $65

Chicago River 90-Minute Architecture Boat Tour

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

(1,655)

from $37

1 to 30 days

3.9

(359)

from $84

Have only a short stay planned in Chicago? Make the most of your time in the Windy City, and see more of the city in less time, when you book a private driving tour of Chicago. Pick between several convenient tour times, and meet your guide and driver directly at your hotel. Over the course of your excursion, you’ll make stops at highlight attractions like the Lincoln Park Conservatory, Millennium Park, and Museum Campus. You’ll also learn about Chicago’s history and can spy other remarkable sights as you go.

Chicago Private Custom City Tour with Hotel Pick Up

3 to 4 hoursFree Cancellation

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.

(204)

from $539

Per group

3 hours 30 minutesFree Cancellation

Chicago Pizza Tour

Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour includes insider stories and landmarks you wouldn't spot on your own—plus a chance to see Windy City icons like the Picasso Statue and Millennium Park.

(471)

from $89

Chicago Architecture Tour: Underground Pedway and the Loop

Chicago Architecture Tour: Underground Pedway and the Loop

Original Chicago Architecture Interiors Tour: Dazzling Interiors

(474)

from $35

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Jean_C, May 2026

fantastic indoor architecture tour

Wonderful tour of indoor architecture; some walking between buildings, so be prepared for weather. Our enthusiastic guide Adam was very knowledgeable and passionate about the places we visited. We learned a LOT about the history of Chicago! He made the tour really fun. The buildings were stunningly gorgeous inside.

Lake Michigan Sunset Cruise in Chicago

Lucy_S, May 2026

A great way to take in...

A great way to take in Chicago’s architecture without walking miles. The sunset tour was absolutely beautiful and totally worth it. I’d recommend arriving about 45 minutes early so you can grab the best seats. Our boat was pretty full, and once we reached the prime photo spots, everyone stood up, which made taking pictures a bit tricky. Overall, I really enjoyed the experience and would highly recommend this tour to anyone visiting the city.

Chicago Architecture River Cruise

Kate_T, May 2026

Interesting + great way to see the city views!

This was a great tour - we learned a lot and our tour guide was very knowledgeable and fun. It was also the perfect length at 1 hour and 15 min. Not too short, not too long. It's a great way to learn more about the history behind Chicago and see the beautiful views!

Chicago Architecture Center River Cruise aboard First Lady

Kathy_K, May 2026

Do this tour!

An essential tour for everyone visiting Chicago (or even locals who want to learn more about Chicago architecture). On a warm day, our sun hats were perfect for sitting upstairs for the entire tour. Wonderful guide with so much great information. Highly, highly recommended!!!

Chicago City Minibus Tour

Fatmata_B, May 2026

This trip was great. He...

This trip was great. He had alot of knowledge about Chicago to pass on and he was very easy to reach. He went far and beyond giving me directions and reaching out on where i should park or how to get to the destination. The tour guy was great and he made it to all the stops even with the traffic that was available .

Chicago Favorites Ultimate Food and Walking Tour

Amanda_F, May 2026

Come Hungry_Leave Full

My daughter and I really enjoyed the tour. The food was excellent. We were lucky to walk next to a Memorial Weekend Parade. Greg was friendly and knowledgeable. The walk was leisurely enough that the Chicago atmosphere could be absorbed. I’m glad we skipped breakfast so that we could come hungry.

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

Margie_U, May 2026

Excellent tour!

Very good tour, plenty of walking and plenty of food. But most importantly, excellent communication from our tour guide, Dash, about what it’s like to live in Chicago now as well as considerable history of the buildings everywhere we went. Entertaining and informative, highly recommend this tour.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Charissa_J, May 2026

Amazing Experience

We had a wonderful experience on this architectural tour. Our guide was fun, engaging, and extremely knowledgeable about the area, which made the ride both enjoyable and informative. I learned so much throughout the tour, and the price was very reasonable for such a great experience.

Chicago Lake and River Architecture Tour

Clint_W, Apr 2026

Perfect Chicago Experience — River + Lake Views in One Trip

Absolutely loved this architecture boat cruise! Getting to see both the Chicago River and Lake Michigan in one trip was the perfect combo. The views of the skyline from the water are incredible, and the guide did a great job sharing interesting history without it feeling overwhelming. Super relaxing, well-organized, and a great way to experience the city—highly recommend!

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 !!!