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.

(10,745)

from $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.

(688)

from $28

from $144

Likely to Sell Out

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

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.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

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.

(3,511)

from $28

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1,893)

from $44

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

(16,826)

from $39

Chicago Hop On Hop Off Open Top Bus Tour

See Chicago your way with flexible hop-on hop-off tickets designed to suit every sightseeing style. Explore the Windy City at your own pace, hopping off to visit top attractions such as Millennium Park, Navy Pier, the Magnificent Mile, and the Chicago Riverwalk while enjoying onboard commentary that adds context to what you see. Perfect for first-time visitors or those short on time, this tour offers flexibility and ensures you don’t miss any of Chicago’s highlights. You can also upgrade your experience to enjoy extra sightseeing time and a panoramic sunset tour for unforgettable skyline views.

Chicago Hop On Hop Off Open Top Bus Tour

Chicago's Navy Pier Centennial Wheel Ticket

3.9

(2,365)

from $49

15 minutesFree Cancellation

4.2

(79)

from $24

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

1 to 4 hoursFree Cancellation

3.9

(1,298)

from $30

Likely to Sell Out

360 panoramic views of the Chicago skyline at sunset.

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

(1,658)

from $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

(1,350)

from $101

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

3 hoursFree Cancellation

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

(2,259)

from $85

360 Chicago Observation Deck Sip and View Ticket

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).

4.1

(108)

from $44

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

4.4

(943)

from $34

Chicago Gangsters and Ghosts Walking Tour

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

Chicago Gangsters and Ghosts Walking Tour

Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture, including Soldier Field and the Shedd Aquarium, as well as the picturesque Lake Michigan shoreline. This unforgettable experience showcases 8 key points of interest along a scenic 10-mile route, perfect for photography enthusiasts and those seeking a unique perspective of the Windy City. - 10-mile scenic helicopter flight over Chicago's skyline - Fly past famous landmarks like Soilder Field and Chinatown - Minimum of 2 passengers required, maximum of 3 per flight - Free parking available at the Vertiport Chicago

(117)

from $38

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

7 to 10 minutesFree Cancellation

4.1

(9)

from $150

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3,490)

from $49

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

3 hoursFree Cancellation

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.

(778)

from $80

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake 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!

(443)

from $47

Chicago River Ghost & Dark History Night Cruise

Chicago River Ghost & Dark History Night Cruise

Chicago Lake and River Architecture Tour

4.1

(182)

from $46

Likely to Sell Out

This tour cruises the Chicago River and Lake Michigan.

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.

(2,418)

from $45

Museum of Ice Cream Chicago Admission Ticket

Museum of Ice Cream Chicago Admission Ticket

45 minutes to 1 hour 30 minutes

3.4

(456)

from $43

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

1 to 30 days

4.0

(365)

from $84

Griffin Museum of Science and Industry Admission

Explore a range of interactive exhibits at the Griffin Museum of Science and Industry in Chicago—one of the largest science museums in the country. Rather than simply viewing displays, enjoy hands-on experiences that bring engineering, technology, and natural science to life. Housed in the last remaining building from the 1893 World's Fair, the museum combines historic significance with immersive exhibits, making it an engaging attraction for visitors of all ages.

Griffin Museum of Science and Industry Admission

2 to 4 hoursFree Cancellation

4.5

(45)

from $26

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Chicago River 90-Minute Architecture Tour

Nicole_M, Aug 2026

City Day!

It was great! Weather was perfect! Great day on the river for a tour. We are from the suburbs and never took the tour but loved it. Recommended for sure. (And thankful the attendants helped me sort out and rebook us on the later tour after I accidentally booked the wrong time slot. )

Chicago Sightseeing River and Lake Cruise

Kyanna_R, Aug 2026

This tour was amazing and...

This tour was amazing and beautiful. 10/10 worth the money. Nice views. The tour guide was extremely knowledgeable on the architecture of Chicago. We got stuck BUUUUT the boat crew remained calm and got us back safely. They gave us a refund before we got back to shore. I would recommend getting new wine because the wine that was there was really nasty lol.

Chicago By Night River and Lake Cruise

Deidre_S, Aug 2026

A great experience

First Lady boat ride was a great experience. You will start on the Chicago river and merge into the Michigan lake. The view was amazing I mean amazing especially at night! The con was it can get a little bit chilly at night so bring a jacket. They sell blankets if you were to get cold and they also have a bar so you can sip and enjoy the ride. I would definitely recommend it.

Chicago Architecture River Cruise

Anjelica_V, Aug 2026

So much fun!!

So great, learned so much. Brian was awesome and actually knows so much about Chicago history. I’m from Chicago and even got a little emotional just to learn so much about the history of our beautiful city. The little photo they do before is so cute. I never usually buy things like that, but it was too cute to pass up. 10/10 experience to say the least. They were also kind enough to rebook my tour as my flights were cancelled and I missed my original booking.

Chicago Lake and River Architecture Tour

Debbie_N, Aug 2026

Fantastic

I’m a Chicagoan myself and did this boat tour and it was nothing but short of spectacular. Spiro our guide was amazing and the tour showed why this city is one of the best cities in the country from views to its history. If you come to Chicago in the Spring, Summer or Fall this should be the first thing you go too.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Katie_T, Aug 2026

Excellent educational tour for all ages

Very educational. We had a group of 8 ranging from 50’s down to a 3 and 4 year old and it was just the right amount of time for them. We did the 9:00 one and John Miller did an excellent job being enthusiastic so early in the morning. Looks as if he truly enjoys his job.

Chicago Favorites Ultimate Food and Walking Tour

Debra_K, Aug 2026

Delicious food and history come together!

This food tour was an excellent combination of delicious Chicago specialties with historical and cultural perspectives. Molly, our guide, shared her well informed perspectives iwith her passion and love for the city. Her storytelling was compelling and entertaining. This tour is a must do and time well spent while you are in Chicago.

Lake Michigan Skyline Cruise in Chicago

Stanley_A, Jul 2026

We had a great experience...

We had a great experience on the Skyline Cruise in Chicago. The staff was extremely friendly and welcoming from start to finish. The boat ride was smooth, and the views of the city were absolutely beautiful. We also enjoyed learning about Chicago’s landmarks and history throughout the tour. I would highly recommend this cruise to anyone visiting Chicago—it’s a relaxing, scenic, and educational experience!

Chicago Architectural River Cruise

Amy_P, Jun 2026

Worth it, honestly.

This boat tour was excellent (and I’ve done a couple in Chicago) staff was pleasant, free soft drinks and lemonade, seating was good. We came very close to leaving time and sat on the side of the boat and was still great. Our tour guide Lynn was extremely knowledgeable and her voice was very pleasant. I would 100% do it again.