All Chicago Tours &amp; Excursions in 2026

Chicago River 45-Minute Architecture Tour from Magnificent Mile

4.7

(3,023)

Free Cancellation
45 minutes

from $28

Likely to Sell Out

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Chicago River 90-Minute Architecture Tour

4.7

(9,727)

Free Cancellation
1 hour 30 minutes

from $45

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.

Chicago Architecture River Cruise

4.8

(15,841)

Free Cancellation
1 hour to 1 hour 30 minutes

from $39

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

Skydeck - Willis Tower Admission

4.3

(1,793)

Free Cancellation
30 minutes to 1 hour 30 minutes

from $44

Marvel at Chicago's iconic architecture and lakefront from a unique perspective with this 30-minute immersive ride. With drone footage, helicopter-mounted cameras, and other custom media, Flyover Chicago creates the sensation of flying above and through the city to take in its highlights from above. Get up close to details atop the highest skyscrapers and learn about Chicago's history and cityscape during the ride.

Free Cancellation
30 minutes

from $38

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

9 days

from $144

Special Offer

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!

Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass

3.9

(2,204)

Free Cancellation
2 hours

from

$41

$45

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

360 CHICAGO Observation Deck Admission

3.9

(1,225)

Free Cancellation
1 to 4 hours

from $30

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!

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.

Chicago Favorites Ultimate Food and Walking Tour

(1,991)

Free Cancellation
3 hours

from $85

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

Lake Michigan Skyline Cruise in Chicago

4.4

(900)

Free Cancellation
30 to 45 minutes

from $33

Chicago Crime and Mob Bus Tour

(3,236)

Free Cancellation
1 hour 30 minutes to 2 hours

from $49

Likely to Sell Out

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

4.5

(1,518)

Free Cancellation
1 hour 30 minutes

from $45

You get to name your new Exclusive Scent

4.8

(52)

Chicago Perfume Making Classes on Magnificent Mile

Free Cancellation
1 hour 15 minutes

from $85

One of the oldest and most iconic franchises in Major League Baseball and a founding member of the National League, the Chicago Cubs’ legacy dates all the way back to 1876. The tradition and heritage is felt throughout Wrigley Field, a hallowed ground amongst baseball fans. The sense of pride and tradition makes every game feel like part of a larger narrative in baseball history. Wrigley Field is one of the most beloved ballparks in the country, offering a charming, old-school baseball experience that’s hard to find elsewhere. Opened in 1914, it’s one of the last remaining "classic" stadiums, with its ivy-covered outfield walls, manual scoreboard, and bleacher seating adding to the nostalgia. The Cubs’ historic 2016 World Series win, snapping their record 108-year drought, is one of the most amazing MLB moments in recent history. The Cubs are a truly iconic team a pioneer of America’s favourite past time. For an MLB experience like no other, Wrigley Field is the place to be!

Chicago Cubs Baseball Game at Wrigley Field

3 hours

from $16

Enter a land of sugar and adventure with admission to Chicago’s Museum of Ice Cream. Immerse yourself in a vibrant world of interactive exhibits, including sprinkle-filled pools, whimsical selfie spots, and exclusive ice cream sampling stations offering seasonal flavors. Whether you’re an art lover or a dessert enthusiast, this playful, family-friendly experience promises fun and memories for all. Avoid disappointment by booking your preferred time.

Museum of Ice Cream Chicago Admission Ticket

3.4

(405)

45 minutes to 1 hour 30 minutes

from $43

Explore the fascinating connection between art and emotions at the EmotionAir exhibition at Balloon Museum. This unique showcase features inflatable art that serves as a mirror to our deepest feelings, allowing visitors to engage with interactive installations, emotional projections, and performance art. First launched in London in December 2023, EmotionAir invites you on a sensory journey that transforms your understanding of art and its emotional impact. Immerse yourself in the intimate nuances of human emotions through this captivating experience.

Balloon Museum Chicago Admission

(8)

1 to 2 hours

from $44

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

Chicago Architecture Center River Cruise aboard First Lady

(5,571)

1 hour 30 minutes

from $57

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

(61)

Free Cancellation
2 hours

from $85

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

Field Museum of Natural History Admission Tickets

(500)

Free Cancellation
4 hours

from $29

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.

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.

Chicago's Chinatown Food and Walking Tour

(613)

Free Cancellation
3 hours

from $80

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

Chicago River Ghost & Dark History Night Cruise

4.0

(105)

Free Cancellation
1 hour 30 minutes

from $46

Total Chicago: From Architecture to Food

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.

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

(1,173)

Free Cancellation
4 hours 30 minutes

from $101

Price varies by group size

3.9

(356)

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

Free Cancellation
1 to 30 days

from $84

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.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

5.0

(1,539)

Free Cancellation
2 hours

from $35

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Top Attractions in Chicago

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What are people saying about Chicago

Field Museum of Natural History Admission Tickets

Julie_C, Mar 2026

Too Much for 1 Day

There is so much to see and explore. Get rest before coming and go see the things you’re interested in first. There is so much to see and experience that it can’t be done in a single day. My kids have very different tastes and we split up. There was something of intense interest for both.

Chicago Favorites Ultimate Food and Walking Tour

Matthew_C, Mar 2026

Great experience

We had a great experience with our guide Wyatt. He was very personable, knowledgeable and was great with our group. The food was very good and a great mix of places that we’ve heard of and places off the beaten path. Also walking through the city seeing the world class architecture was another great part of the tour.

Chicago River 90-Minute Architecture Tour

Leen_K, Mar 2026

I highly recommend!

What a lovely experience! Chicago's architecture really is remarkable and this company called Wendella did such a fantastic job at showing us that. Our tour guide was named David I believe and he was so funny and informational. He shared some very interesting historical background on the city and the buildings. Even though it was raining most of the time on the cruise, you are free to stay on the top floor or go down to the second floor where it's warm and you can get snacks or drinks like a hot chocolate. This is one of those experiences you must do in Chicago, especially if it's your first time. There's nothing like it!

Chicago Architecture River Cruise

Marty_R, Mar 2026

Great tour on a perfect day!

What a great tour on a gorgeous day! We lucked out with the weather for sure —- 70 degrees and sunny! Perfection. Our guide (I think his name was Victor— I’m terrible with names) was fantastic! Very knowledgeable about all of the architecture, designers, and timelines. He is a native Chicagoan, so he definitely knew his stuff! It was interesting to hear of the history and what had been in some places before. He had photos of the former structures and had some of the ones that were being built. So well worth the time and great value, imo. The boat itself was very nice - not too big and not too small. There was a nice restroom on the first level, and a well kept bar with good selection of beverage options. I didn’t see as many people tipping as I felt should have because our guide was absolutely incredible. Of course it’s always optional, but I felt he definitely went the extra mile.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Jezier_P, Feb 2026

Cool experience

My first time and honestly I enjoyed it. We learned some interesting cool facts about the buildings and Riverwalk. And the view was simply amazing. I booked the 5:30 tour so we could view the sundown and lights at night and it didn't disappoint. Its definitely a cool experience and the 45 minutes go by fast.

Chicago Crime and Mob Bus Tour

Danielle_K, Jan 2026

A fun tour

My boyfriend and I were visiting Chicago and decided to do the Crime and Mob Boss tour. Our guide, Dane, was a bit goofy and playing the showman, but it was still very educative. The small pamphlets he handed out at the beginning also helped. We got to see in daylight the parking lot that was the site of the St. Valentine's Day Massacre. (Yes, there was duplication between the tours, but I don't mind.) You stop at the Biograph Theatre, where John Dillinger was killed, and you can take photos of a mural dedicated to him. One of the Harry Caray Steakhouse locations has a mini mob museum that is a stop. You get to hear about Leopold and Loeb, two young men who decided to commit a murder for fun. It's more grim history of Chicago. I had a great time and definitely recommend it.

Flyover in Chicago

Krystal_M, Jan 2026

Flyover with friends

I had an incredible time! I feel like every city should have something like this! We got to experience the whole city without actually stepping foot in some of the cities most highlighted landmarks. Of course we would actually want to see but our short time here would not permit. This was the next best thing you could do. Definitely recommend 10/10

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

chloe_b, Dec 2025

Thank you leslie <3

Leslie made our experience wonderful! We celebrated my girlfriend’s birthday by doing the brunch. Even though it was raining, it was still beautiful! Leslie made sure that our mimosas were filled, the staff was very friendly, and food was delicious. We will definitely be back for another brunch or dinner!

Chicago Architecture Center River Cruise aboard First Lady

Fu_Y, Nov 2025

I’m really glad I took...

I’m really glad I took the tour. It’s a great way to spend 90 minutes if you want to learn more about Chicago during a short trip. The guide was fantastic, she knew so much about Chicago’s history, especially the river, the bridges, and the buildings. The bar was great too: warm and cosy, and a perfect place to enjoy a couple of beers with friends. You won’t regret it.

Chicago Architectural River Cruise

Patricia_A, Oct 2025

Tour to remember

A fantastic tour from start to finish thanks to Staff. Crew and Superb guide. One of the best Viator tours we have tsken over the year and our first in Chicago and provided so much background information about the city 😀! Talented. Professional and knowledgeable Guide made the tour astounding as she provided history. Hearsay and Art and Architectural information. ENJOYED HER HUMOR and Candid perspective as a native and highly educated and experienced individual. THANK YOU to all the staff, who made us feel welcome and provided courteous and friendly customer service to all. Kudos !

Lake Michigan Sunset Cruise in Chicago

Lauren_T, Oct 2025

Our tour guide, John, was...

Our tour guide, John, was full of energy and provided plenty of knowledge about Chicago history while making it a fun environment. The music was a variety of genres so there is something for everyone. We didn’t purchase any beverages while on the cruise, but they did let us know it was available. Worth the money for sure! Picture worthy.