What Are the Top Things to Do in Chicago in Winter?

Are you planning a trip to Chicago in the winter? If so, you’re in for a treat! The Windy City offers a variety of activities and attractions that are perfect for the colder months. Whether you’re a fan of outdoor adventures or prefer indoor experiences, Chicago is sure to have something for everyone. In this article, we’ll explore the top things to do in Chicago in winter, so you can make the most of your trip.

Ice Skating in Millennium Park

One of the most iconic winter activities in Chicago is ice skating in Millennium Park. Located in the heart of downtown, Millennium Park offers a picturesque ice skating rink with a stunning view of the city skyline. Whether you’re a beginner or an experienced skater, this is a must-do activity during your visit to Chicago. Lace up your skates and glide across the ice as you take in the beauty of the surrounding architecture.

Visit the Art Institute of Chicago

If you’re looking for an indoor activity to escape the cold, the Art Institute of Chicago is a fantastic option. This world-renowned museum is home to an extensive collection of artworks, including masterpieces by artists such as Van Gogh, Monet, and Picasso. Explore the galleries and immerse yourself in the beauty of art. The museum also offers guided tours and educational programs for visitors of all ages.

Explore Navy Pier

Navy Pier is a popular destination year-round, and winter is no exception. This iconic Chicago landmark offers a wide range of entertainment options, including restaurants, shops, and attractions. Take a ride on the Ferris wheel for a stunning view of the city, or visit the Winter WonderFest, a holiday-themed indoor amusement park. Navy Pier is a hub of activity, and there’s always something exciting happening.

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Enjoy a Show at the Chicago Theatre

Chicago is known for its vibrant performing arts scene, and winter is the perfect time to catch a show at the historic Chicago Theatre. From Broadway musicals to stand-up comedy performances, there’s something for every taste. The theater itself is a work of art, with its stunning marquee and glamorous interior. Sit back, relax, and enjoy an evening of entertainment in one of Chicago’s most iconic venues.

Go Shopping on the Magnificent Mile

If you’re in the mood for some retail therapy, head to the Magnificent Mile. This famous stretch of Michigan Avenue is lined with luxury boutiques, department stores, and flagship stores. From high-end designer brands to popular retailers, you’ll find it all here. Even if you’re not looking to shop, strolling along the Magnificent Mile and admiring the beautiful architecture is a must-do activity in Chicago.

Savor Chicago’s Culinary Delights

Winter is the perfect time to indulge in Chicago’s famous culinary scene. From deep-dish pizza to gourmet hot chocolate, there’s something to satisfy every palate. Explore the city’s diverse neighborhoods and discover hidden gems. Whether you’re in the mood for comfort food or want to try something new, Chicago has an abundance of restaurants and foodie experiences waiting to be explored.

Take a Tour of the Skydeck Chicago

No visit to Chicago is complete without a trip to the Skydeck at Willis Tower. Soar 1,353 feet above the city and enjoy breathtaking views of Chicago’s skyline, Lake Michigan, and the surrounding area. If you’re feeling brave, step out onto The Ledge, a glass balcony that extends four feet outside the building. This thrilling experience is not for the faint of heart but is definitely worth it for the incredible views.

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Experience Chicago’s Festive Spirit

Winter in Chicago is a magical time, and the city comes alive with holiday cheer. From festive events to dazzling light displays, there’s no shortage of holiday spirit. Don’t miss the annual Christkindlmarket, a German-inspired market filled with unique gifts and delicious treats. Take a walk around the city and admire the beautifully decorated storefronts and twinkling holiday lights. Chicago truly knows how to celebrate the season.


Chicago offers a wide range of activities and attractions during the winter months. Whether you’re interested in outdoor adventures or prefer indoor experiences, the Windy City has something for everyone. From ice skating in Millennium Park to exploring the art at the Art Institute, there’s always something to see and do. So bundle up, embrace the cold, and enjoy all that Chicago has to offer this winter.

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