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Things to Do in Chicago this Winter

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129 Reviews
Things to Do in Chicago this Winter
The Windy City may be famous for its snowfall, but don’t let that dissuade you from visiting. Chicago transforms into a winter wonderland during the cold months. Explore its holiday light displays, visit its festive markets, and enjoy cozy stints in the city’s museums and speakeasies. Here’s how to plan the perfect winter getaway to Chicago.

  • Pair a visit to the sky-high Willis Tower Skydeck with a Chicago-style pizza meal.
  • Visit some of the Windy City’s coziest and most atmospheric speakeasies during a Prohibition-themed tour.
  • When the weather is frightful, enjoy an indoor day at the Field Museum of Natural History, Art Institute of Chicago, or Adler Planetarium.
  • Visit Christmas markets, skating rinks, and other seasonal attractions during a holiday stroll and food tour.
  • View the Windy City from the sky during a ride in a helicopter that’s been decorated with holiday lights.
  • Discover the city’s holiday light displays by trolley, private vehicle, or Segway.
  • Plan a New Year’s Eve to remember by booking a luxury dinner cruise on Lake Michigan.
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3 Tours and Activities | All Chicago Tours

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Chicago Prohibition Tour

Chicago Prohibition Tour

star-4.5
Visit four historic bars in operation since Prohibition in Chicago, and learn from a knowledgeable guide about the surreptitious world of the speakeasy. This adults-only tour takes you by coach to once-illicit establishments in Old Town, Wicker Park and the Chicago Loop where liquor, jazz and mobsters ruled. You’ll hear about Chicago gangsters like Al Capone and learn the historical context for the decade-long ban of alcohol. If you’d like, you can purchase recommended craft cocktails and signature drinks of the 1920s.
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  • 3 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$55.00
From
$55.00
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

2-Hour Chicago Holiday Lights Segway Tour

2-Hour Chicago Holiday Lights Segway Tour

star-4.5
Soak up the Windy City’s festive holiday feel and explore local landmarks with ease on this Segway tour in Chicago. Hop onto your Segway and spin through Chicago’s Millennium Park to the Loop. With your guide, you'll watch skaters enjoying the ice rink, explore Michigan Avenue and admire festive department store displays. See the German Christmas market stalls at Daley Plaza, where locals sip hot chocolate and munch 'bratwurst,' and enjoy the atmosphere beneath the city’s Christmas tree. Get the personalized feel of a small-group experience.
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  • 2 hours to 2 hours 15 minutes
  • Free Cancellation
From
$75.10
From
$75.10