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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, 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.
Did you know?You can reserve your spot today and pay when you're ready.
Learn more
Did you know?
You can reserve your spot today and pay when you're ready.Learn more
4 Tours and Activities
Holiday Hike Chicago-Style: Festive Food & Walking tour
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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From
HK$642.13
From
HK$642.13
Field Museum of Natural History Admission Tickets
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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From
HK$216.75
From
HK$216.75
Chicago New Year's Eve Buffet Dinner Cruise on Lake Michigan
Celebrate New Year’s Eve in Chicago with a 4-hour dinner cruise on Lake Michigan, an evening of dining, dancing, and spectacular views. You’ll set sail from Navy Pier aboard a luxurious cruiser, enjoy a freshly-prepared buffet dinner and dessert bar, then get the party started with a top Chicago DJ. This 4-hour New Year’s Eve cruise includes dinner, entertainment, and a Champagne toast at midnight, with the option to upgrade for a private table and open-bar access.
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From
HK$2,193.62
From
HK$2,193.62
New Year's Eve Plated Dinner Cruise on Lake Michigan
Board a luxury yacht for a 4-hour dinner cruise on New Year's Eve in Chicago. Choose to be seated in the rooftop lounge or explore the well-appointed ship before sitting down for a 3-course, gourmet meal. Relax with tea and coffee while taking in views of the skyline or dancing to the onboard DJ.
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From
HK$2,742.15
From
HK$2,742.15