Winter Activities in Chicago: The Best Things to Do

Ice Skating in Millennium Park

Few winter experiences in Chicago are as iconic as ice skating at Millennium Park, where the McCormick Tribune Ice Rink welcomes skaters from November through March. Against the breathtaking backdrop of the Chicago skyline and Cloud Gate (The Bean), gliding across the ice feels like stepping into a winter wonderland. Skating is free, though rentals are available for those without their own gear. For a more dynamic experience, head to the Maggie Daley Park Skating Ribbon, a winding ice path that weaves through a scenic, tree-lined landscape, offering a one-of-a-kind way to enjoy the season.

Beyond Millennium Park, Chicago boasts several other enchanting ice rinks. The Rink at Gallagher Way, near Wrigley Field, provides a festive, family-friendly setting, while the Sky Rink at The Peninsula Hotel offers a luxurious rooftop experience with stunning city views. Neighborhood rinks run by the Chicago Park District provide a local, community-focused option for those looking to skate away from the crowds. For visitors staying at Fairmont Chicago - Millennium Park, the park rink is just steps away, making it a perfect home base for a winter getaway in the Windy City.

Christmas Lights and Displays: Where to See the Best Decorations

When winter arrives, Chicago transforms into a dazzling spectacle of twinkling lights and festive displays, turning the city into a true holiday wonderland. From millions of glowing bulbs to immersive winter experiences, the season brings a magical energy that fills the streets. Among the most breathtaking displays, Lincoln Park ZooLights enchants visitors with over 2.5 million LED lights, 3D installations and synchronized festive music, creating a mesmerizing holiday atmosphere. Over on Michigan Avenue, the Magnificent Mile Lights Festival kicks off the celebrations in November, featuring a brilliant parade, fireworks and miles of illuminated storefronts.

For those seeking a more immersive experience, Illumination at Morton Arboretum turns towering trees into a kaleidoscope of color, blending nature and technology in a breathtaking outdoor setting. Meanwhile, Light Up the Lake at Navy Pier offers an indoor winter escape, featuring interactive light displays and ice skating under a sea of glowing installations. Staying at Swissôtel Chicago, you will be near the Magnificent Mile, making it easy to experience the best Christmas decorations in the city.

Exploring Chicago’s Winter Festivals

Winter in Chicago is anything but quiet, as the city comes alive with festivals that celebrate the season through food, music and holiday magic. The beloved Christkindlmarket, held in Daley Plaza, transports visitors to a European-style Christmas village, where handcrafted gifts, mulled wine and traditional bratwurst create a festive, old-world charm. Over at Navy Pier, Winter WonderFest transforms an indoor space into a holiday playground, complete with an ice rink, carnival rides and seasonal attractions. Food lovers can indulge during Chicago Restaurant Week, a culinary event in January and February featuring prix fixe menus at top restaurants across the city. For those who love the outdoors, Polar Adventure Days at Northerly Island offers a unique winter escape, where visitors can snowshoe, meet Arctic animals and explore the beauty of Chicago’s winter landscape. With so many exciting events, the cold never stops the city from celebrating the season in style.

Indoor Attractions: Museums, Theaters and More

For those looking to escape the cold, Chicago’s vibrant indoor attractions provide endless ways to explore the city while staying warm. Art lovers can spend hours at the Art Institute of Chicago, home to world-renowned masterpieces, while science enthusiasts will be captivated by the interactive exhibits at the Museum of Science and Industry, including the enchanting Christmas Around the World display. The Field Museum, with its ancient artifacts and the iconic Sue, the world’s most famous T. rex, offers a journey through history unlike any other. For a truly immersive experience, 21c Museum Hotel Chicago is not just a place to stay but a contemporary art museum in itself, featuring thought-provoking exhibitions alongside stylish accommodations. With world-class museums, theaters and cultural spaces, Chicago proves that winter is the perfect time to explore its indoor treasures.

Dining Experiences: Cozy Restaurants and Hot Chocolate Spots

After a frosty day exploring Chicago, few things are more satisfying than a comforting meal or a decadent cup of hot chocolate. The city’s dining scene offers plenty of warm, inviting spaces, from cozy gastropubs to world-class fine dining. The Gage, a stylish spot near Millennium Park, pairs hearty dishes with the warmth of a crackling fireplace, while Geja’s Café sets the scene for romantic fondue dinners, perfect for a cold winter evening. For a truly unforgettable culinary experience, Alinea takes dining to an art form, offering immersive, multi-course creations that make any winter night special.

When it comes to warming up with something sweet, Katherine Anne Confections serves luxuriously thick, handmade hot chocolate, while XOCO, Rick Bayless’s beloved café, is famous for its authentic Mexican hot chocolate. Over at Mindy’s Bakery, rich cocoa topped with fluffy homemade marshmallows makes for the perfect winter indulgence. Whether savoring a comforting meal or a velvety cup of hot chocolate, Chicago’s cozy dining spots make winter even more inviting.

Shopping in Chicago During Winter: Malls and Holiday Markets

Winter in Chicago brings a magical shopping experience, blending luxury boutiques, iconic department stores and festive holiday markets. Along the Magnificent Mile, shoppers can explore a world-class mix of high-end brands, flagship stores and stylish boutiques, making it the ultimate destination for fashion lovers and gift seekers alike. Just steps away, Water Tower Place offers a sprawling indoor shopping mall, ideal for browsing in warm comfort while discovering a variety of retailers. For those looking for one-of-a-kind, handcrafted gifts, the Christkindlmarket is a holiday favorite, filled with traditional German ornaments, artisanal crafts and seasonal treats. Guests staying at Sofitel Chicago Magnificent Mile will find themselves in the heart of the city’s premier shopping scene, just moments away from Chicago’s best winter retail experiences.

Outdoor Adventures: Snowshoeing, Sledding, and More

For those who embrace winter’s crisp air and snowy landscapes, Chicago offers plenty of outdoor adventures beyond the city’s urban charm. At Northerly Island, snowshoeing trails provide a peaceful escape, allowing visitors to explore scenic lakefront views and serene natural beauty. Thrill-seekers can head to Soldier Field, home to one of the best sledding hills in the city, where families and friends race down the snow-covered slopes. For a more immersive winter experience, the Cook County Forest Preserves offer miles of cross-country skiing trails, winding through tranquil woodlands and open fields, making it a perfect way to enjoy Chicago’s winter wonderland.

Best Places to Visit Near Chicago in Winter

For a picturesque winter escape just beyond Chicago, several nearby destinations offer scenic beauty, seasonal charm and outdoor adventure. Lake Geneva, Wisconsin, transforms into a snowy retreat, featuring skiing, ice castles and cozy lakeside resorts perfect for a winter weekend getaway. Nature lovers can head to Starved Rock State Park, where frozen waterfalls and scenic hiking trails create a breathtaking winter landscape. For a mix of history and seasonal charm, Galena, Illinois, enchants visitors with quaint streets, boutique shopping and festive holiday lights, making it an idyllic cold-weather retreat just a short drive from the city.

What to Do in Chicago in December, January and February

Each winter month in Chicago brings its own seasonal magic, offering a mix of festive celebrations, culinary experiences and outdoor fun. December sparkles with holiday lights, the beloved Christkindlmarket and ice skating in Millennium Park, creating a storybook winter atmosphere. As January arrives, the city keeps the energy alive with Chicago Restaurant Week, where food lovers can indulge in exclusive prix fixe menus, while winter sports and snowy adventures provide the perfect way to embrace the season. By February, romantic Valentine’s Day dining experiences and indoor attractions like museums and theaters offer warm escapes from the chilly weather, ensuring that winter in Chicago remains vibrant and exciting from start to finish.

How to Get Around Chicago in the Winter

Navigating Chicago in winter is seamless, thanks to a variety of transportation options that keep the city moving—even in snowy conditions. The CTA trains and buses provide a budget-friendly and reliable way to travel, connecting major attractions and neighborhoods with ease. For a more direct and flexible option, taxis and rideshares are readily available, though prices can surge during snowstorms and peak hours. Downtown visitors can also take advantage of Chicago’s network of heated skywalks, which link many buildings, hotels and shopping centers, offering a warm and convenient way to explore the city on foot.

Accor Hotels: Comfortable Stays for Your Winter Trip

Make your Chicago winter getaway even more memorable with a cozy, stylish stay at an Accor hotel, where comfort, convenience and prime locations come together seamlessly. After a day of ice skating, winter festivals, or holiday shopping, unwind in elegant rooms, enjoy fine dining and take in breathtaking city views from the comfort of your hotel.

No matter how cold it gets, Chicago’s winter charm never fades—and with Accor, your stay will be just as unforgettable. Join ALL – Accor Live Limitless today to enjoy exclusive member perks, special offers and rewarding travel experiences year-round.