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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.