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Things to Do in Chicago this Winter

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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.
  • Spend hours exploring the interactive exhibitions at the Museum of Science and Industry.
  • 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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Chicago Tours & Activities (5)
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Chicago Prohibition TourHistorical & Heritage Tours

Chicago Prohibition Tour

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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
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  • Free Cancellation
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$45.00 
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  • 3 hours 30 minutes
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  • Free Cancellation

Willis Tower Skydeck LunchAttraction Tickets

Willis Tower Skydeck Lunch

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Enjoy lunch above the clouds at the Willis Tower, where authentic Chicago-style pizza is paired with unforgettable views of the Chicago skyline. Customize your own perfect pizza from a list of gourmet ingredients, then select a salad and a traditional Italian dessert. Capture unforgettable images from the dining room on the 99th floor, then continue to The Ledge, a glass floored balcony perched near the top of America’s tallest building.
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  • 2 hours
  • Free Cancellation
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$95.00 
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  • 2 hours
  • Free Cancellation

Field Museum of Natural History AdmissionMuseum Tickets & Passes

Field Museum of Natural History Admission

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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
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$26.00 
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  • 8 hours
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Holiday Hike Chicago-Style: Festive Food & Walking tourChristmas

Holiday Hike Chicago-Style: Festive Food & Walking tour

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Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.
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  • 3 hours
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  • Free Cancellation
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$69.99 
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  • 3 hours
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  • Free Cancellation

2 HR Chicago Holiday Lights Segway TourSegway Tours

2 HR Chicago Holiday Lights Segway Tour

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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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  • 120 to 135 minutes
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  • Free Cancellation
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$75.10 
From  
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  • 120 to 135 minutes
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  • Free Cancellation


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