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54 results | All Chicago Tours

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Chicago Architecture River Cruise
Likely to Sell OutLikely to Sell Out

Chicago Architecture River Cruise

star-5
6988
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour
  • Free Cancellation
From
$40.33
From
$40.33

90-Minute Chicago River Architecture Tour

90-Minute Chicago River Architecture Tour

star-4.5
1343
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
175
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 in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
2180
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
562
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$40.00
From
$40.00

Lake Michigan Sightseeing Cruise
Likely to Sell OutLikely to Sell Out

Lake Michigan Sightseeing Cruise

star-4.5
329
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
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  • 30 minutes
  • Free Cancellation
From
$26.16
From
$26.16

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
915
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
From
$26.10
From
$26.10

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4.5
1143
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$46.00
From
$46.00

30 Minute Lake Michigan Speedboat Ride

30 Minute Lake Michigan Speedboat Ride

star-4.5
123
Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.
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  • 30 minutes
From
$34.75
From
$34.75

Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate
Likely to Sell OutLikely to Sell Out

Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate

star-5
27
Feel the rush of skydiving without going anywhere near a plane, with this indoor skydiving experience in Chicago. Start off with thorough training so you feel confident and know what to expect. Then, enjoy two 60-second ‘free fall’ experiences in a technologically advanced vertical wind tunnel, which feels much like real skydiving. No experience is necessary, and your instructor will give you hands-on assistance when you need.
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  • 1 hour 15 minutes
From
$92.64
From
$92.64

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate
Likely to Sell OutLikely to Sell Out

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

star-4
11
Discover the adrenaline rush of skydiving without setting foot on a plane at iFly Chicago-Rosemont. Offered 9am to 10pm, you can easily find a session that fits with your busy schedule. Feel confident after a small-group training session, then head into the tunnel for your solo floats.  An instructor is present for both 60-second sessions to give you personalized instruction. Afterwards, take home a flight certificate to commemorate your adventure.
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  • 1 hour 15 minutes
From
$86.69
From
$86.69

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

star-5
2
Aviation fanatics can take to the skies and try flying an actual helicopter with this Schaumburg flight experience that's perfect for first-timers. You enjoy helpful advice from your instructor before taking the controls on a flight that whisks you past Sears Centre Arena, Woodfield Mall, and Boomers Stadium. With free parking, noise-canceling headphones, and one-on-one attention from the pilot, this beginner-friendly experience is a near-perfect way to try flying for yourself.
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  • 30 minutes
  • Free Cancellation
From
$295.00
per group
From
$295.00
per group

Chicago CityPASS

Chicago CityPASS

star-4.5
335
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 Shedd Aquarium, Skydeck Chicago (Opening with reimagined experience in Spring 2021), and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
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  • 9 days
  • Free Cancellation
From
$109.00
From
$109.00

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
Likely to Sell OutLikely to Sell Out

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
334
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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  • 4 hours
  • Free Cancellation
From
$84.99
From
$84.99

Chicago Skyline Tall Ship Cruise

Chicago Skyline Tall Ship Cruise

star-4.5
189
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs.
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  • 1 hour 15 minutes
From
$44.00
From
$44.00

Chicago Premier Dinner Cruise on Lake Michigan

Chicago Premier Dinner Cruise on Lake Michigan

star-3.5
159
Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.
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  • 2 hours 30 minutes
From
$158.98
From
$158.98

Bike Tour of Chicago's Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
150
Pedal past the lakefront neighborhoods of Chicago's North Side on this bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
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  • 3 hours
  • Free Cancellation
From
$49.99
From
$49.99

45-Minute Chicago River Architecture Tour from Magnificent Mile
Likely to Sell OutLikely to Sell Out

45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
143
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.
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  • 45 minutes
  • Free Cancellation
From
$23.00
From
$23.00

Chicago Lunch Cruise on Lake Michigan
Likely to Sell OutLikely to Sell Out

Chicago Lunch Cruise on Lake Michigan

star-4
84
Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.
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  • 2 hours
From
$81.46
From
$81.46

Chicago's West Side Foodie Ride Bike Tour

Chicago's West Side Foodie Ride Bike Tour

star-5
82
Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.
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  • 4 hours
  • Free Cancellation
From
$79.99
From
$79.99

The Escape Game Chicago: Epic 60-Minute Adventures

The Escape Game Chicago: Epic 60-Minute Adventures

star-5
77
Located in River North, these adventures offer a one-of-a-kind premium experience. Follow clues and solve puzzles to complete your mission together. You might escape...You WILL have fun! Choose to play one of five uniquely immersive games: - Gold Rush: Find hidden gold in the California hills! - Prison Break: Complete a daring escape from the evil warden! - Special Ops: Mysterious Market: Uncover the truth as a secret agent! - The Heist: Recover a stolen masterpiece from an art thief! - Mission: Mars: Launch your spaceship from the Red Planet!
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  • 1 hour 15 minutes
  • Free Cancellation
From
$41.41
From
$41.41

Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

star-5
54
Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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  • 3 hours
  • Free Cancellation
From
$49.99
From
$49.99

Chicago Family Food & Bike Tour with Top Attractions

Chicago Family Food & Bike Tour with Top Attractions

star-5
46
See Chicago light up with a 4-hour bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in daytime or evening views of Millennium Park and the Museum Campus. Sample culinary classics of Chicago, like deep-dish pizza, a true Chicago hot dog, and a tasty dessert for good measure. Upgrade your experience to enjoy a locally crafted beer pairing at three of the food stops. As you pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.
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  • 4 hours
  • Free Cancellation
From
$74.99
From
$74.99

Private 45-Minute Chicago Skyline Helicopter Tour

Private 45-Minute Chicago Skyline Helicopter Tour

star-5
40
Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.
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  • 45 minutes
  • Free Cancellation
From
$849.00
per group
From
$849.00
per group

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