All Chicago Tours &amp; Excursions in 2026

Chicago River 90-Minute Architecture Tour

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.

(10,310)

from USD 45

30 minutesFree Cancellation

Flyover in Chicago

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.

(611)

from USD 28

from USD 144

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

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1,855)

from USD 44

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

(3,326)

from USD 28

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

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.

4.5

(1,599)

from USD 45

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

(1,289)

from USD 101

Chicago's Navy Pier Centennial Wheel Ticket

15 minutesFree Cancellation

4.2

(69)

from USD 24

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

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,402)

from USD 39

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

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!

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

The best views of Chicago can be yours at 360 Chicago Observation Deck! Perched 94 stories above the Windy City in the former John Hancock Building, 360 Chicago provides commanding views of Lake Michigan and Chicago’s towering skyscrapers. 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. *TILT not included in purchase

3.9

(2,299)

from USD 49

360 Chicago Observation Deck Sip and View Ticket

Chicago 3D Fireworks Cruise

4.1

(96)

from USD 44

See Chicago's magnificent skyline at night!

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.

4.2

(242)

from USD 52

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

3.9

(1,270)

from USD 30

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

30 to 45 minutesFree Cancellation

4.4

(927)

from USD 33

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,390)

from USD 49

Museum of Ice Cream Chicago Admission Ticket

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

45 minutes to 1 hour 30 minutes

3.4

(432)

from USD 43

Chicago River Ghost & Dark History Night Cruise

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

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.

4.1

(143)

from USD 46

Field Museum of Natural History Admission Tickets

4 hoursFree Cancellation

4.6

(540)

from USD 29

Skyline Queen showcasing the Chicago Skyline!

See the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline, offering a unique perspective of towering skyscrapers and historic architecture. This tour offers stories about the city’s history and culture as you pass by Chicago's landmarks, museums, and buildings. Capture unforgettable images of the city skyline from Lake Michigan, ensuring a unique look at Chicago, perfect for all ages.

Chicago Sightseeing River and Lake Cruise

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.

(610)

from USD 46

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.

5.0

(1,703)

from USD 35

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

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.

(350)

from USD 47

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

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

(724)

from USD 80

1 to 30 days

4.0

(361)

from USD 84

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.

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

Chicago By Night River and Lake Cruise

(2,150)

from USD 85

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Seth_P, July 2026

Night Cruise On The Lake and River

The Chicago By Night River and Lake Cruise was outstanding. The director of the tour was funny, very knowledgeable and engaging. The boat was clean and the bartenders were skilled. The organizers were professional and I really enjoyed my time. I’m glad I did it

Chicago River 90-Minute Architecture Tour

Richard_s, June 2026

Tess was outstanding,...

Tess was outstanding, informative and wonderful. The tour was amazing and will do again! It would be quite helpful, since not many people carry cash anymore, to have a Venmo or QR code on display to leave a tip for any of your guides. I heard other passengers express the same, as we wanted to leave Tess, our guide, a gratuity for all her kindness and hard work.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

QUINTINA_M, June 2026

Great experience

I must commend the highly engaging experience, largely attributed to the exceptional performance of our guide. My only concern pertains to the accessibility of the vessel. As an individual with a disability, I encountered significant difficulty navigating the boarding stairs. I regret not having been informed in advance about the absence of alternative access options. But all and all it was a GREAT EXPERIENCE!

Chicago Crime and Mob Bus Tour

Victor_C, June 2026

Great tour by our guide, Tess.

Great tour with lots of information on the beautiful Chicago River. Tess, our tour guide, was great and covered a lot of ground (water?) in a short amount of time. Our boat was full and we had to sit on the side which was not ideal -- get there at least 15-20 minutes before departure time to get a good seat.

Chicago Architecture Center River Cruise aboard First Lady

Leslie_Y, June 2026

The only architectural tour to consider

This is the only tour to consider when looking for an architectural boat tour. I accidentally booked on another company. On that day, the surroundings were not familiar and I fortunately was able to book on the first lady that day. Dr. Mark. (?) [a retired orthopedic surgeon] was our docent. I have lived in Chicago for over 70 years and last year was my first tour on the first lady. It certainly won’t be my last.

Chicago Favorites Ultimate Food and Walking Tour

Christina_L, June 2026

Jessika was an incredible...

Jessika was an incredible tour guide, super bubbly and knowledgeable! I am from Chicago, but my roommate was in town from Ann Arbor. It was still so cool to hear about the history of my own city, and get to eat at local but not super well known places. It was the perfect mix of walking and eating so I didn’t feel overly full at the end. Overall great experience!!

Chicago Sightseeing River and Lake Cruise

REGINA_E, June 2026

Good choice for cruise

River cruise into Lake Michigan with an amazing guide who knew the entire history of Chicago. He points out a lot of buildings and other sights. Before you can go into the lake you have to wait for the water to settle which is interesting in itself. You will have a great view of Chicago from the water.

Lake Michigan Sunset Cruise in Chicago

Cindi_B, June 2026

Gorgeous sunset views!!

Gorgeous sunset views! (We never actually saw the sunset…) A sister trip that was just magical! Between the sites, the refreshments, and the company, was just perfect! Note: THIS IS NOT AN ARCHITECTURE TOUR! The poor tour guide said it three times and people still asked, lol! She was hilarious too though, very entertaining!!

Chicago Architecture River Cruise

Ladiny_P, June 2026

A nice tour around Downtown Chicago

Booked this experience last minute to see the sites that downtown Chicago has to offer. The tour was only an hour, but time really flew by. Unfortunately, due to the other passengers having side conversations, I barely was able to hear the guide explain the different buildings and its significance. Overall a great experience.

Lake Michigan Skyline Cruise in Chicago

Anisha_S, June 2026

Relaxing Ride

The skyline tour was exactly what I needed after a day of eating and walking about. I was able to book the tour an hour before, which worked for my itinerary and it was affordable. I liked that it is a double decker boat and got to experience the tour from top deck. The day was beautiful and perfect for a tour. The boat was clean, looked presentable, offered cocktails and small snacks(for purchase) and staff were friendly. The tour offered ok views. I was able to capture pictures of the Chicago skyline. My fav part of the ride was how relaxing it was. I would do it again and be sure to nap the next time lol.