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Chicago Tours

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Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
4607
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). From Memorial Day to Labor Day (May 29 - September 6,) each ticket includes a one-way water taxi ticket.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$38.15
From
$38.15
Taking safety measures

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

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

star-5
9
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
  • Taking safety measures
From
$92.64
From
$92.64
Taking safety measures

360 CHICAGO Observation Deck Admission (Hancock Center)

360 CHICAGO Observation Deck Admission (Hancock Center)

star-4.5
221
Tower above the Windy City’s world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird’s-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline, and enjoy a variety of educational exhibits on site. Upgrade your ticket to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. Or, choose the Sun and Stars package for two visits to the observation deck within 48 hours. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.
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  • 1 day
  • Free Cancellation
  • Taking safety measures
From
$25.00
From
$25.00
Taking safety measures

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

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

star-5
240
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 the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. 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
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

Spray Paint 'n' Sip at Studio W.I.P.

Spray Paint 'n' Sip at Studio W.I.P.

star-4.5
10
Native 312 offers a unique spin on BYOB paint night! Join us as we host an intimate look into the world of Urban Art as we learn about some different styles and techniques with guest artists. Then you get your hands dirty as you walk around our gallery setting and test out your skills in different mediums like aerosol spray and stencil. At the end of your workshop you will be able to go home with your own piece of art!
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$40.00
From
$40.00
Taking safety measures

Chicago Loop Walking Tour

Chicago Loop Walking Tour

star-5
25
Step into the heart of Chicago with this 2-hour walking tour of the Loop. You’ll meet your local guide at the Chicago Cultural Center and make your way through the city’s downtown. Stop to check out the elevated “L” train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You’ll come away with a deeper sense of Chicago’s rich history and architecture.
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  • 2 hours
  • Free Cancellation
From
$42.67
From
$42.67

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

star-5
4
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
  • Taking safety measures
From
$86.69
From
$86.69
Taking safety measures

Chicago Crime and Mob Bus Tour

Chicago Crime and Mob Bus Tour

star-4
737
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
  • Taking safety measures
From
$45.00
From
$45.00
Taking safety measures

Bike Tour of Chicago's Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
128
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
  • Taking safety measures
From
$49.99
From
$49.99
Taking safety measures

Ultimate Chicago Food Tour by Bike

Ultimate Chicago Food Tour by Bike

star-5
35
See Chicago light up at night with a 3-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 evening views of Millennium Park and the Museum Campus. 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
  • Taking safety measures
From
$72.99
From
$72.99
Taking safety measures

Millennium Park Photo Shoot and Walking Tour

Millennium Park Photo Shoot and Walking Tour

star-5
3
On this two-in-one tour, you won’t just discover Chicago’s highlight public park: you’ll also do so in the company of a professional photographer, who will capture portrait shots as you explore. Pick from multiple daily tour times, and meet your private guide at Millennium Park. You can look forward to seeing park highlights like Anish Kapoor’s "Cloud Gate" sculpture (better known as “The Bean”), Lurie Garden, Maggie Daley Park, Buckingham Fountain, and more. Following the tour, receive high-quality digital photos of your experience.
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  • 30 minutes to 2 hours
  • Free Cancellation
  • Taking safety measures
From
$150.00
per group
From
$150.00
per group
Taking safety measures

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-4.5
1166
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
  • Taking safety measures
From
$27.00
From
$27.00
Taking safety measures

2-Hour Chicago Fireworks Segway Tour

2-Hour Chicago Fireworks Segway Tour

star-5
10
Experience Chicago like never before on this guided, 2-hour, small-group Segway tour. Visit popular Grant Park and see Buckingham Fountain’s breathtaking, evening light show, with an illuminated Windy City skyline as the perfect backdrop. Glide along the lakefront, then witness Chicago's weekly summer fireworks display at Navy Pier from a secret location. Guided Segway training plus the use of a helmet are included. Dress in weather-appropriate clothes with flat, closed-toed shoes.
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  • 2 hours
  • Free Cancellation
From
$75.58
From
$75.58

Learn to Make Chicago Deep-Dish Pizza with a Local

Learn to Make Chicago Deep-Dish Pizza with a Local

star-5
4
Up your culinary skills and take the tastes of Chicago home with you at a 3-hour small-group cooking class. Using provided ingredients and under the careful guidance of your teacher, learn to prepare the city’s most famous dish from scratch. Once your personal deep dish pizza is out of the oven, tuck in and wash it down with a local PBR beer.
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  • 3 hours
  • Free Cancellation
From
$53.85
From
$53.85

Tandem Skydiving Experience in Chicago

Tandem Skydiving Experience in Chicago

star-5
29
Go skydiving in Indiana at a location situated only a 1-hour train ride from Chicago, making it easy to reach without a car. Your instructor provides all necessary equipment and training for your jump, then accompanies you on the tandem skydiving experience from 14,000 feet (4,267 meters). See Lake Michigan and perhaps the Chicago skyline from the air, and purchase video and photos of your jump if you wish.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$209.00
Price varies by group size
From
$209.00
Price varies by group size
Taking safety measures

Chicago City Minibus Tour with Optional Architecture River Cruise

Chicago City Minibus Tour with Optional Architecture River Cruise

star-4.5
357
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside neighborhoods. You have a chance to get out and visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.
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  • 2 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$39.95
From
$39.95
Taking safety measures

Skip the Line: Tommy Gun's Garage Dinner and Show Ticket

Skip the Line: Tommy Gun's Garage Dinner and Show Ticket

star-4.5
206
Transport yourself back in time to Chicago’s roaring twenties at Tommy Gun’s Garage, a unique speakeasy dinner show in the Windy City. Say the password at the front door and then step into an era of mob guys and flappers, Broadway tunes by Cole Porter and George Gershwin and lively dances like the Charleston. This gut-busting show, full of song, dance and audience participation, is sure to please.
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  • 3 hours
  • Free Cancellation
From
$68.72
From
$68.72

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

Go Chicago Explorer Pass with SkyDeck and 360 Chicago

star-4.5
197
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Go Chicago Explorer Pass saves you up to 45 percent on regular ticket prices. Create your own sightseeing itinerary by choosing 2, 3, 4, or 5 attractions, tours, and activities from among more than 30 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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  • 60 days
From
$66.00
From
$66.00

Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

star-5
36
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
  • Taking safety measures
From
$49.99
Price varies by group size
From
$49.99
Price varies by group size
Taking safety measures

Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour

Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour

star-4.5
40
Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.
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  • 1 hour 15 minutes
  • Free Cancellation
From
$40.46
From
$40.46

Navy Pier Photo Shoot and Walking Tour

Navy Pier Photo Shoot and Walking Tour

star-5
1
Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -1 or 2-hour private session with a professional, local photographer -High-resolution edited images delivered via a private online gallery within 24-48 hours
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  • 1 to 2 hours
  • Free Cancellation
From
$200.00
per group
From
$200.00
per group

Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

star-5
69
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
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

2-Hour History of Chicago Architecture and Art Segway Tour

2-Hour History of Chicago Architecture and Art Segway Tour

star-5
13
Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
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  • 2 hours
  • Free Cancellation
From
$75.10
From
$75.10

2-Hour Chicago Lakefront and Museum Campus Segway Tour

2-Hour Chicago Lakefront and Museum Campus Segway Tour

star-5
67
Explore Chicago by Segway with the benefit of a scenic 7- or 8-mile tour led by your guide. Start with an orientation to operating the Segway and a few minutes to practice. Then roll through the paths of Grant Park to Buckingham Fountain and glide along the Chicago lakefront to view attractions such as Museum Campus, Shedd Aquarium, The Field Museum, and Soldier Field, homefield for the Chicago Bears.
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  • 2 hours
From
$73.24
From
$73.24

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