All Chicago Tours &amp; Excursions in 2026

Chicago River 90-Minute Architecture Tour

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

(1,321)

from US$27

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

Special Offer

Chicago River 90-Minute Architecture Boat Tour

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

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

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

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 US$144

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.

360 panoramic views of the Chicago skyline at sunset.

Lake Michigan Sunset Cruise in Chicago

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

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

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

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

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.

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

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

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

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

Discover one of the Windy City’s most spooky, gruesome destinations when you book advance tickets to the Medieval Torture Museum. Perfect for Halloween—or any other creepy-crawly occasion—this museum includes a wealth of information about medieval torture practices and devices, plus realistic models to add a macabre edge. Book tickets before you travel for a seamless visiting experience, and make use of an audio guide and included ghost-hunting app.

Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

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

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

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

(118)

from US$44

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

Original Chicago Architecture Interiors Tour: Dazzling Interiors

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

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago Architecture River Cruise

Tamsin_N, Oct 2026

Highly recommend

Great experience. There are wonderful views from the boat and our guide (Victor) was very informative and entertaining with his storytelling and historical facts. The architecture tour really brought the history of Chicago to life through the changing structures and styles of the buildings.

Lake Michigan Sunset Cruise in Chicago

michelle_m, Oct 2026

Solo Vacation Week -KCMO Visitor

I have always wanted to have a fun adventure. My bucket list of my things to do includes riding the Subway Train, Boat Ride on Lake Michigan as the Sun sets and be Solo. It's been a challenging year for me. I lost a family member, a personal friend and a professional colleague of mine. This is my way of honoring my friends and family and celebrating them.

Chicago River 90-Minute Architecture Tour

Arlene_B, Oct 2026

Do NOT miss this on your trip to Chicago!

This Architectural Tour is MUST see when you come to Chicago. It's been about 10 years since I've done it and it never disappoints! You always learn something new and the views are spectacular -- ones you can't get, unless you're on the water. Worth every penny! Plus our tour guide, Spiro, was fabulous!!!

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Brenda_N, Oct 2026

Take the tour.

It was a fun experience. Give yourself extra time to find the appropriate meeting spot… There are a lot of similar tours in that area. There are limited shaded spots on the boat. The torque gives great views of the city, informative commentary about the surrounding buildings and a nice vantage point of the Riverwalk.

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!

Flyover in Chicago

Angela_S, Sept 2026

Flying rollercoaster of fun around downtown Chicago

If you’re good with heights and motion, it is an AMAZING experience and way to see downtown Chicago. I recommend doing Flyover after you’ve been around downtown. day or two so you recognize some of the buildings as you fly. The one thing that would make it better is if they had a little better customer service and communicated about the number of stairs or even verbally offered an elevator option instead of just ushering everyone to the stairs. There are already a lot of stairs in Chicago so taking what seemed like 2-3 flights of stairs (as in going down to the L) was a surprise. The ride made up for this. It was so cool to fly all around the riverfront and downtown area. At one point, I put my hands in the air because it felt like we were on a rollercoaster drop. So much fun!

Chicago Sightseeing River and Lake Cruise

Jack_H, Sept 2026

The best part of Chicago

We did a tour guided by Cole yesterday and he did a fantastic job. His energy kept the tour entertaining and upbeat. You obtained a great deal of history involving the water system, the architecture and more while enjoying all the wonderful views. We had the option of sitting inside or outside. We also enjoyed some beverages from the bar and the bartender was also pleasant. I highly recommend the boat tour when you visit Chicago.

Chicago River 90-Minute Architecture Boat Tour

Angela_S, Sept 2026

Wonderful Architectural River Tour

I would absolutely recommend this tour to anyone who enjoys fun. Our tour guide, Tila, was informative, fun and hilarious. I learned so much about Chicago’s architecture and history, and how much the people of Chicago love this beautiful city. Take a drink, make sure your phone is charged and enjoy!

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