All Chicago Tours &amp; Excursions in 2026

Chicago River 90 Minute Architecture 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

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

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

(1 328)

from US$27

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 Hop-on Hop-off Sightseeing Tour by Open-top Bus

2 hoursFree Cancellation

Chicago's Navy Pier Centennial Wheel Ticket

15 minutesFree Cancellation

Most Chicago sightseeing tours focus on the city’s key landmarks. But on this unique excursion, you cam dig deeper than surface level, and discover some of the city’s spookiest stories. Pick between private or shared options, and set off to explore the South Loop with your guide. Along the way, see where notorious gangsters like Al Capone operated, hear about their bloody backstories, and even visit several of the state’s most haunted addresses.

Chicago Gangsters and Ghosts Walking Tour

2 hoursFree 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

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

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

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 River 90-Minute Architecture Boat Tour

Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.

Chicago By Night River and Lake Cruise

Chicago Perfume Making Classes on Magnificent Mile

1 hour 15 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

Chicago Architecture and True Crime: Halloween Edition

1 hour 30 minutes to 1 hour 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

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

Many Chicago architecture tours focus on the city’s famous buildings—but few actually venture inside the landmarks. On this shared or private tour, step right inside many of the city’s top architectural icons, discovering sights and details that few other travelers get to see. Visit the legendary Rookery, explore the Chicago Cultural Center, view Tiffany glass ceilings and art deco highlights, and much more.

Chicago's Secret Interiors Architectural Walking Tour

2 hoursFree Cancellation

Price varies by group size

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

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

1 to 30 days

4.0

(370)

from US$84

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Must-Dos in Chicago

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What are people saying about Chicago

Chicago By Night River and Lake Cruise

Charde_Y, Nov 2026

The Tour We Didn’t Know We Needed

Do not leave Chicago without booking this tour!!! My friends and I visited Chicago for the first time ever this past week and this was the first experience we signed up for. There was an issue on our part with scheduling and we appreciate the company for accommodating us because we enjoyed every single moment of the cruise! You’ll have plenty of time to capture your experience through your camera lens, but to also just enjoy the moment through your own eyes. The lady tour guide was funny! 10/10. We’ll see you all again when we’re back in Chicago!

Chicago River 90 Minute Architecture Tour

Jansen_E, Nov 2026

Amazing Tour Guide – Educational and Fun!

Justine was an amazing tour guide! She was incredibly knowledgeable, engaging, and made the entire experience both educational and fun. As a 7th-grade math teacher, she has a natural talent for making learning interesting and interactive. Her creativity, enthusiasm, and sense of humor really brought the tour to life. I had a wonderful time and would definitely recommend her to anyone looking for a fun and memorable experience!

Flyover in Chicago

Willie_P, Nov 2026

Great Experience

Flyover is an indoor simulated flying experience at Navy Pier. You're suspended in moving seats in front of a massive curved screen, with wind, mist, sound, and other effects making you feel like you're soaring over Chicago Incredible views of Chicago's skyline and landmarks. Feels similar to Disney's Soarin' ride. Great indoor activity when Chicago weather is cold. Exciting visuals and realistic motion effects.

Chicago Favorites Ultimate Food and Walking Tour

Jessica_S, Oct 2026

Biggest Bang for Your Buck

A great way to pack a day’s worth of food and history into a few hours. Food? Delicious! Tour? Awesome! Guide? Epic! Cassandra (Caddie) brought the history of Chicago’s food, architecture, and art to life with her energetic and entertaining delivery. She was friendly and funny, making the hours fly by. As a solo traveler I was made to feel part of the group which was so comforting. I also can’t wait to take a bike ride around the river and lake with the included bike rental! This tour really packs in so much bang for your buck! 20/10 Highly Recommend!

Chicago Architecture Center River Cruise aboard First Lady

Mary_M, Oct 2026

Absolutely lived up to the hype!

An exceptional tour from start to finish. We took the 11:00 AM slot and had perfect weather, which made for stunning photos of the skyline. The CAC docent was fantastic, delivering a masterclass in Chicago history and architecture without it ever feeling dry. The boat was spacious, clean, and very well-run. Booking through Viator was seamless. Don't look at any other boat tours—this is the official one you want to choose.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Jeanine_O, Oct 2026

Fabulous way to spend an evening!

The night cruise along Chicago River was awesome. Kay, our tour guide was knowledgeable and funny and made the 45 minutes fly by! What was a happy surprise was that ALL passengers had a seat up top. Looked like so many, but they did it right. I would do it again during the day as well to see the contrast. Great value for your your dollar!

Chicago River 90-Minute Architecture Boat Tour

Chris_S, Oct 2026

David is the best in the city!

This was an excellent tour. The the ride was comfortable, though. I would’ve liked something a little bit better than folding chairs, but everybody had space it was a very stable comfortable ride. David was absolutely fantastic. I cannot say enough good things about him as the tour guide. His knowledge was excellent. His timing was fantastic. He was personable. He was funny. If I come back, I’ll probably go see him again even though it will be a repeat experience because he was just that enjoyable highly recommend 10/10

Chicago Lake and River Architecture Tour

Gregory_L, Oct 2026

Great experience on the river

This is the second time we have experienced the architectural river tour. Learned new stuff and the crew aboard the boat was friendly and accommodating as they were the last time. This is definitely an interesting and economical experience for anyone who lives here and wants to learn more of Chicago’s history or someone from out of town that just wants a nice afternoon. !