All Chicago Tours &amp; Excursions in 2026

Chicago River 90 Minute Architecture Tour

1 hour 30 minutesFree Cancellation

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

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

Price varies by group size

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

(1,327)

from USD 27

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

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

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

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

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

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

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

Museum of Illusions Chicago Admission Ticket

45 minutes to 1 hour 30 minutes

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

Chicago's Navy Pier Centennial Wheel Ticket

15 minutesFree 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

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

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

Chicago River 90-Minute Architecture Boat Tour

1 hour 30 minutesFree 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

Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighborhoods, and waterfront views. The flight begins near the Chicago Fire Practice Facility before heading over Chinatown, where colorful architecture and historic streets create a striking aerial view. From there, you’ll pass McCormick Place, the largest convention center in North America, stretching along the lakefront and highlighting the scale of Chicago’s downtown footprint. Continuing north, you’ll fly over Northerly Island and Soldier Field, followed by the heart of the Museum Campus, where the Field Museum and Adler Planetarium sit against the backdrop of Lake Michigan. Grant Park comes into view next, often called Chicago’s front yard, leading to an aerial look at Millennium Park and the unmistakable curves of The Bean.

Chicago Helicopter Tour: Loop Tour

12 to 15 minutesFree Cancellation

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

7 to 10 minutesFree 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

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

1 to 30 days

4.0

(370)

from USD 84

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

Voted the #1 Immersive Art Experience in America by USA Today readers in 2024, Color Factory Chicago celebrates the joy of color. Guests embark on a bright and colorful journey through 14+ immersive installations that inspire joy and human connection, expand boundaries of perception, encourage play, and engage the senses in unexpected ways. Fun for all ages, each visit includes surprise giveaways, sweet treats, and complimentary digital photos. From the lobby to the gift shop and every colorful moment in between, our spaces are as inclusive as they are dynamic and celebratory. Each room is designed in partnership with an exceptional roster of local and international artists and collaborators. Jump into color with us! Please note: At least ONE person's ID must match the name on ONE ticket. If no one in your party has an ID matching the name on one ticket, you will not be allowed entry. Minors under the age of 18 will not be allowed inside without a parent or guardian.

Color Factory Chicago Ticket

1 hour to 1 hour 30 minutes

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago Gangsters and Ghosts Walking Tour

Avery_W, Oct 2026

Do iiiiiit

This experience was probably one of the best parts of our trip. We were so surprised. Tanner was really engaging with his story telling, he made you want to keep listening and learn about the history of Chicago. I would highly recommend this to anyone that loves history and/or Chicago. We really loved our experience. Give Tanner a raise!!!!!!

Chicago Favorites Ultimate Food and Walking Tour

Ramona_M, Oct 2026

What better way to become familiar with Chicago

The tour guide was incredibly knowledgeable about the city’s architect and was so understanding in making sure our needs were met during the tour. The food was absolutely great! My favorite was the Chicago dog, remember? When in Rome, do as the Romans do! Don’t ask for ketchup on a Chicago dog! 😂

Flyover in Chicago

Kamieria_T, Oct 2026

The Kams over Chicago

At first I was scared and nervous but then I was like this is cool. My boyfriend loved it and we might do it again. My only knit pick was how long it took to board the ride but great time flying over Chicago lol I had one eye open it felt to real for me

Chicago River 90 Minute Architecture Tour

Lauryn_L, Oct 2026

10/10 experience

John was our tour guide and made the experience. He was super funny and knowledgeable. The sunset was beautiful and it wasn’t too cold this time of year. It didn’t feel like the ride was too long or too short either. Amazing views, and they let you get up to take photos towards the end. It was a great way to start our trip.

Chicago By Night River and Lake Cruise

Gloria_S, Oct 2026

Beautiful sunset boat ride

This night boat ride was amazing! We took the 6:30 boat, and seeing Chicago at night, and the shoreline was magical. The boat went down the river slowly with narration the whole time. Matthew was very knowledgeable, and we leaned many things we never knew about the history of Chicago. We also went through the locks out to the lake, and had a smooth ride along the shoreline, and Matthew pointed out different buildings along the way! Bring a warm coat or blanket if it's cool out- and enjoy the ride! We would definitely recommend this !

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Stephanie_T, Oct 2026

Best night of my life… why did I wait so long

I would happily recommend this attraction to guest and visitors.. it’s affordable.. calming.. education and fun for fellowship with people and the tour guide was simply amazing.. his knowledge of our downtown history was so fulfilling..can’t wait to do it again

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

Rachel_G, Oct 2026

Cool experience and take your dogs if you can!

This was a really cool experience and a great way to see the Chicago River and the Chicago skyline. The history was interesting and Mac our guide was great and super informative. We traveled with our 2 dogs and the boat was gentle enough that you barely felt like you were moving. Money well spent!

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 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!