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Local Experiences in Chicago

Local Experiences in Chicago

The Windy City is a destination of icons—famous foods, sports teams, architectural wonders, and historic blues bars. It’s a multifaceted metropolis with a lot going on, both on and off the tourist path. Here are a few ways to experience Chicago like a local.

Highlights

  • Hit the waters of Lake Michigan during aprivate sailing excursionalong Chicago’s stunning lakefront.

  • Explore Chicago’s top-notch craft beer scene with a ride on theBrewery Barrel Bus.

  • Grab a paddle and gokayaking at twilightto watch the fireworks over Navy Pier.

*Skip the line at one of Chicago’s top museums, including the Art Institute of Chicago, Alder Planetarium, Museum of Science and Industry, or Field Museum.

  • Indulge in a favorite Chicago pastime—retail therapy—with ashop and spa tour along the Magnificent Mile.

*Rent a bikeand hit the pavement for a self-guided tour of Chicago’s vibrant and diverse neighborhoods.

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

13 Tours and Activities | All Chicago Tours

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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
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
$67.00
From
$67.00

Chicago-Naperville Indoor Skydiving with 2 Flights & Personalized Certificate

Chicago-Naperville Indoor Skydiving with 2 Flights & Personalized Certificate

star-3.5
Experience the thrill of skydiving, without jumping out of a plane, in a vertical wind tunnel.  Offered every half hour from 9am to 10pm, you can easily find a time slot that works for you. After small-group training, enjoy two solo sessions in the tunnel during which you float atop wind speeds as fast as 175 mph (282 kph). Feel secure with a guide giving you one-on-one coaching during each 60-second session.
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  • 1 hour 15 minutes
  • Taking safety measures
From
$69.95
From
$69.95
Taking safety measures

Field Museum of Natural History Admission Tickets

Field Museum of Natural History Admission Tickets

star-4.5
Delve deep into the world of natural history with this Field Museum admission ticket in Chicago. Spend as long as you like exploring the museum's collection of more than 26 million artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Time travel through 13,000 years of history in the Americas, from the Ice Age to Inca and Aztec temples. Take advantage of the free daily tours, led by Field Museum docents.
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  • 8 hours
  • Free Cancellation
  • Taking safety measures
From
$26.00
From
$26.00
Taking safety measures

Chicago Odyssey Dinner Cruise

Chicago Odyssey Dinner Cruise

star-4
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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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$108.66
From
$108.66
Taking safety measures

Chicago Craft Brewery Barrel Bus Tour

Chicago Craft Brewery Barrel Bus Tour

star-4.5
Learn about Chicago’s brewpub scene and taste different types of craft beer on this guided brewery tour. Visit unique breweries for craft beer samples plus an additional brewing production facility for an in-depth tour. Discover the science behind the brewing process, complete with step-by-step procedures, and enjoy plenty of beer samples throughout the tour. Round-trip transportation in a Prohibition-era-styled barrel bus is included.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$89.60
From
$89.60
Taking safety measures

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$427.28
per group
From
$427.28
per group
Taking safety measures

LEGOLAND Discovery Center Chicago 2 Hr. Playtime Session

LEGOLAND Discovery Center Chicago 2 Hr. Playtime Session

star-3.5
Bring the kids to  LEGOLAND® Discovery Center in Schaumburg for a day of brick-building adventure. With 30,000-square-feet of space this family-friendly attraction has activities for everyone: from an interactive pirate-themed playland to a factory tour where you can actually see how LEGO bricks are made. There's even a mini replica of famous Chi-town landmarks made from nearly 2-million LEGO pieces.
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  • 7 hours
  • Free Cancellation
  • Taking safety measures
From
$20.96
From
$20.96
Taking safety measures

Transfer to Chicago Premium Outlets

Transfer to Chicago Premium Outlets

star-5
Spend a day shopping at the premier name brand shopping destination in the Chicago metro area, Chicago Premium Outlets. Featuring prominent international and American designer brands at discounted prices, you'll find deep discounts at stores like Nike, Armani, Calvin Klein, Kate Spade, 7 for All Mankind, and much more inside the outlet mall. The tour includes pickup and drop-off from Chicago hotels and five hours of on-the-ground shopping time.
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  • 7 hours
  • Free Cancellation
From
$288.00
per group
From
$288.00
per group

Chicago Bike Rental

Chicago Bike Rental

star-5
Discover Chicago's many delights from the comfort of two wheels. Simply pick up your full-day bike rental with lock, map and helmet and start exploring, either solo or with friends. Make your way through Millennium Park and to historic Wrigley Field, stop for a visit at Navy Pier or spend a couple hours watching sea turtles, penguins and even a piranha at Shedd Aquarium. You get to tour Chicago independently at your own pace and leisure without having to deal with parking or public transit.
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  • 1 day
  • Free Cancellation
  • Taking safety measures
From
$25.99
From
$25.99
Taking safety measures

Skip the Line: American Writers Museum Admission Ticket

Skip the Line: American Writers Museum Admission Ticket

star-5
Immerse yourself in American literary traditions, and enjoy a host of interactive exhibitions, during a visit to Chicago’s one-of-a-kind American Writers Museum. Conveniently located on Michigan Avenue, the museum was established in 2017, and is one of the city’s newest highlight institutions. Guarantee your admission, and prevent any travel hassles, by securing your tickets in advance. Once inside, you’ll have time to explore at your own pace.
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  • 1 to 5 hours
  • Taking safety measures
From
$14.00
From
$14.00
Taking safety measures

Volo Auto Museum: Admission Ticket

Volo Auto Museum: Admission Ticket

star-4.5
Take a stroll through the history of automobiles at the Volo Auto Museum, just outside Chicago. Car enthusiasts, families, and history buffs will all find something fascinating to discover at the museum. It is spread over 35 acres, with 33 exhibits to explore. See the classic cars, vintage bikes, exhibits devoted to trains, military vehicles, campers…even Batmobiles and Mickey Mouse.
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  • 1 to 5 hours
  • Free Cancellation
From
$19.95
From
$19.95

Tandem Skydiving Experience in Chicago

Tandem Skydiving Experience in Chicago

star-5
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 River Kayak Tour

Chicago River Kayak Tour

star-4.5
Set your paddle into the Chicago River on a leisurely 2.5-hour kayak tour past the skyscrapers of downtown Chicago. Both novice and experienced kayakers will be at ease on this excursion past sights such as the Civic Opera Building and the Marina City Towers. Hear fascinating tales of the Windy City as you gaze at a stunning architectural landscape from the water, just how the original Chicago natives originally navigated the area!
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  • 2 hours 30 minutes
  • Free Cancellation
From
$0.00
From
$0.00