All Chicago Tours &amp; Excursions in 2026

Chicago River 90 Minute Architecture Tour

1 hour 30 minutesFree Cancellation

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.

30 minutesFree Cancellation

Flyover in Chicago

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.

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

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.

from USD 144

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

Chicago Gangsters and Ghosts Walking Tour

Price varies by group size

Chicago's Navy Pier Centennial Wheel Ticket

15 minutesFree Cancellation

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

(1,326)

from USD 27

Discover more of Chicago beyond downtown with this convenient South Side open-top shuttle transfer. Travel from central Chicago to some of the city’s most important cultural and historic destinations, including Jackson Park, the Obama Presidential Center campus, and the Griffin Museum of Science & Industry. Enjoy an easy ride south without arranging taxis, rideshares, or public transit connections. The shuttle first stops near the Obama Presidential Center and Jackson Park, giving you access to one of Chicago’s most historic lakefront spaces. Explore the area at your own pace, take photos, or continue your visit independently. The route also serves the Griffin Museum of Science & Industry, one of Chicago’s most popular attractions and one of the largest science museums in the world. This is a great option for travelers who want a simple, affordable way to visit Chicago’s South Side highlights from downtown. Choose a one-way transfer or an all-day ticket for added flexibility.

Roundtrip Shuttle to South Side and Obama Presidential Center

Roundtrip Shuttle to South Side and Obama Presidential Center

30 minutesFree Cancellation

Special Offer

Chicago River 90-Minute Architecture Boat Tour

1 hour 30 minutesFree Cancellation

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 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.

Chicago Architecture River Cruise

1 hour to 1 hour 15 minutesFree 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.

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

4 hours 30 minutesFree Cancellation

Price varies by group size

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

360 Chicago Observation Deck Sip and View Ticket

4.0

(119)

from USD 44

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

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

Chicago Skyline Snap Tour Helicopter Flight Over Chicago

7 to 10 minutesFree Cancellation

Step into the captivating realm of illusions, where reality is never exactly as it appears. Museum of Illusions is a one-of-a-kind, visual, sensory, and educational experience designed to engage your sense of wonder and challenge perceptions through the science behind optical illusions. We offer over 50 immersive, hands-on exhibits to explore. Our illusion rooms, installations and holograms let you defy gravity, grow and shrink your body, walk into a life-size kaleidoscope, and play tricks on your senses at every turn. It’s a mind-bending journey that deceives the senses and reveals how the brain interprets reality.

Museum of Illusions Chicago Admission Ticket

45 minutes to 1 hour 30 minutes

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

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

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

1 hour 30 minutesFree Cancellation

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

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

4 hoursFree Cancellation

We invite you to step inside the city’s most exclusive, jaw-dropping architectural treasures. Led by an expert local storyteller, you’ll discover breathtaking hidden spaces, from Frank Lloyd Wright’s sunlit masterpiece inside the Rookery to the world's largest Tiffany stained-glass domes at the Cultural Center and Marshall Field Building. Walk through the stunning Gilded Age luxury of the Palmer House and iconic movie backdrops along La Salle Street at a relaxed, conversational pace. We combine world-class history with photo vantage points, ending with personalized local recommendations. Don’t just see Chicago, experience it from the inside out.

Chicago's Secret Interiors Architectural Walking Tour

Price varies by group size

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

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

1 to 30 days

4.0

(370)

from USD 84

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Cheryl_E, Oct 2026

It was evening and...

It was evening and drizzly/rainy. The buildings could not always be seen as they drifted in and out of clouds (magical and mysterious). The tour guide also shared lots of fun trivia and history. It was my two teen children's favorite Chicago experience. Highly recommend!

Chicago River 90 Minute Architecture Tour

Marijo_H, Oct 2026

Exceptional tourist experience.

A must see if you are new to Chicago or haven't been here for a few decades. John was an informative, entertaining guide. We are Senior travelers, and we appreciated the easy accessibility and comfort of this boat trip. Afterward you can enjoy any of the wonderful restaurants in that neighborhood.

Flyover in Chicago

Sonya_L, Oct 2026

The title I would give my review would be "Don't Stop Believing"

So actually this is our hometown me and my husband we still reside here however, this was our first time. From the beginning until the end I love how we were given a presentation and the breakdown of what our beautiful city Chicago is like. And how we are believers and how we strive to make it and keep pressing. We reeeeaaaaallly enjoyed the Fly Over part it was so amazing we will definitely be back I can't believe it took us this long to do this the customer service was amazing as well everything was tip too notch quality.Agaun we will be back thank you all so much for your hospitality.

Chicago Architecture Center River Cruise aboard First Lady

Anonymous, Oct 2026

First Lady Experience

Beautiful cruise & excellent docent Bob. We were a party of 16 including architectural professors (UIC) & students on a field trip visiting from Atlanta. We were disappointed however that the South end of the River was inaccessible due to bridge construction. This was to be an important part of the students cruise. Wish we had been advised when purchasing tickets.

Chicago Sightseeing River and Lake Cruise

Nahrain_C, Oct 2026

Beautiful Chicago Experience

The boat guided was wonderful. The narration of Chicago's architectural history was interesting and informative. Everyone on board was friendly and accommodating. My only drawback was that it was not handicap accessible (not that I saw, anyway). Taking 2 flights of stairs down and then up again afterward is not easy for seniors or people with leg injuries/medical issues.

Chicago Architecture River Cruise

Sofii_M, Oct 2026

Review

Absolutely amazing experience! The Chicago Architecture Boat Tour was one of the highlights of our visit. The staff was incredibly friendly, and our tour guide shared accurate information and fascinating stories in such an entertaining way. We learned so much about Chicago’s architecture and history while enjoying beautiful views of the city. I 100% recommend this tour to anyone visiting Chicago! It’s a must-do experience! 🚤🏙️✨

Chicago By Night River and Lake Cruise

Ravi_V, Oct 2026

It was a really good...

It was a really good experience. It got a bit cold when we got to Lake Michigan, but that was expected. It was great to listen to the history of the awesome architecture in Chicago. Anna, our guide was fantastic. She was extremely articulate and kept the tour interesting and funny at the same time. Cheers!

Chicago River 90-Minute Architecture Boat Tour

Sharolyn_B, Oct 2026

The dock is a bit run...

The dock is a bit run down. There are at least porta-potties. The seating on top of the boat is folding chairs, but pretty comfy ones. But the tour guide was just amazing! So knowledgeable, and he gave a really good mix of historical facts, interesting happenings, Chicago culture, and humor. Very enjoyable!

Chicago Crime and Mob Bus Tour

Su_O, Sept 2026

Best Crime Tour in Town

Our first time in Chicago and my daughter really wanted to see the crime tour. We had an amazing time driving thru Chicago and listing to the stories. We stopped in 3 locations and was able to get out of the bus and explore. See the actual "crime scene" We did it on Sunday morning, so traffic and places were not as crowded. TOTALLY WORTH IT

Chicago Lake and River Architecture Tour

Tamara_P, Sept 2026

This was a perfect ...

This was a perfect activity for anyone who loves to see the history of Chicago and experience the beauty of the outdoors on the river and lake., we loved it , the tour guide was not only knowledgeable but funny as well ! We enjoyed it and would recommend anyone to do this trip it was about and 1 1/2 hours which was the perfect amount of time .highly recommend!