“Baby, it’s cold outside” -but don’t let the winter blues stop you from experiencing fun and unique winter activities in Chicago.
Whether you’re ice-skating under bright lights or sampling wine and cocktails at a local bar, there are plenty of unique activities to embrace the chilly season. There are so many fun things to do in Chicago, especially during the colder months.
Check out these 20 fun and exciting things to do in Chicago this winter and make your stay in the city unforgettable!
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Fun Winter Activities In Chicago
Outdoor Adventures: Things to Do Outdoors This Winter in Chicago
Practice ice skating in Chicago Parks
Glide across the ice in the shadow of Chicago’s iconic skyline downtown or a neighborhood rink. Ice skating is a popular winter activity in Chicago that offers a fun-filled experience for all ages. Most rinks in Chicago are free and open from November to March, plus visitors can rent ice skates on-site. This winter activity is perfect for a romantic date or a family outing.
Take a journey through snow-covered trails snowshoeing at Northerly Island
Escape the hustle and bustle of the city by snowshoeing at Northerly Island. It’s a serene winter wonderland with breathtaking views of Lake Michigan. This secluded island offers a peaceful retreat from the city, with plenty of snow-covered trails to explore. Visitors can rent snowshoes on-site and enjoy a leisurely hike through the snow, taking in the stunning lake views and winter scenery.
Explore Chicago’s architectural history on a heated boat tour
Discover Chicago’s stunning architecture from the comfort of a heated boat. The Chicago River looks even more enchanting with a dusting of snow. The architectural boat tour is a popular winter activity in Chicago, offering visitors a chance to learn about the city’s history and architecture while staying warm and cozy on a boat. The tour takes visitors through downtown Chicago, showcasing some of the city’s most famous buildings and landmarks.
Walk among snow-covered trees at an arboretum or state park in Illinois
Illinois is home to many beautiful state parks and arboretums, which offer a peaceful retreat from the city during the winter months. Visitors can take a leisurely walk through the snow-covered trees, enjoying the serene winter scenery. Some popular parks and arboretums in Illinois include Starved Rock State Park, the Morton Arboretum, and Matthiessen State Park.
Indoor Escapes: Cozy Winter Activities in Chicago
Practice self-care with a winter wellness retreat
Treat yourself to a winter wellness retreat at one of Chicago’s spas. Relax and rejuvenate with a soothing massage or a rejuvenating spa day. Experience the ultimate relaxation and pampering at one of Chicago’s world-class spas. From hot stone massages to aromatherapy, these spas offer a variety of treatments to help you unwind and de-stress. You can find popular spas located throughout downtown Chicago and the suburbs. Use services like Resort Pass to book a day pass or spa services in advance and ensure a hassle-free experience.
Rent a romantic resort room or cozy cabin in a popular Midwest town
If you are looking for a winter getaway, consider renting a comfortable cabin or room in a luxury hotel located in a small, yet popular Midwest town. We recently stayed at the Abbey Hotel in Lake Geneva and had an amazing time. Several other destinations in the Illinois, Wisconsin, and Michigan areas offer a variety of winter activities, such as skiing, snowboarding, snowshoeing, and ice tubing. After a day on the slopes, visitors can unwind in their cozy lodging of choice, complete with the most relaxing amenities.
Enjoy your favorite tunes at a winter concert
Take a look at the winter concert lineup in Chicago. Whether you’re a fan of holiday classics or contemporary performances, there’s something for everyone. There are several popular venues in the city for winter concerts, and you can find some of the best ones listed here.
Cozy Up at a Speakeasy
Chicago has its fair share of hidden gems. Warm up with a craft cocktail at one of the city’s many speakeasies, each with its unique charm. Speakeasies were popular during the prohibition era, and many of these hidden bars have been restored to their original glory. Visitors can enjoy a cozy atmosphere, live music, and delicious cocktails at speakeasies in popular nightlife neighborhoods.
Watch live performances at Chicagoland theaters
Chicago is home to a thriving theater scene, with many theaters offering live performances throughout the winter months. From Broadway shows to improv comedy, visitors can enjoy a variety of performances in the city. Some of the most popular theaters in Chicago include the Chicago Theater, Black Ensemble Theater, and Cadillac Palace.
Cultural Experiences: Unique Winter Activities
Celebrate Black History Month in February, and all year long
February is Black History Month, and Chicago offers many events and activities to celebrate the contributions of African Americans to American history and culture. Visitors can attend lectures, art exhibits, film screenings, and more throughout February and beyond.
Shop at a winter farmers’ market
Explore a winter farmers market in Chicago and savor seasonal produce, artisanal goods, and gourmet treats from local vendors. An indoor winter farmers market is a great Chicago winter activity that supports local farmers and artisans. Most markets take place during the weekend during the winter months, offering a variety of vendors selling everything from fresh produce to artisanal cheeses.
Shop small and local in a Chicago neighborhood
Support local businesses and shop small by exploring one of Chicago’s many neighborhoods. Each neighborhood has its unique charm and offers a variety of shops and restaurants to explore. Some popular neighborhoods for shopping in Chicago include Wicker Park, Lincoln Park, and Andersonville.
Cheer for the Bulls or Blackhawks at the United Center
Chicago is home to two major sports teams, the Bulls and the Blackhawks, both of which play at the United Center. Visitors can cheer on their favorite team while enjoying the excitement and energy of a live game. The United Center is also home to various concerts and events throughout the winter months.
Dine out during Chicago Restaurant Week
Sample the best menus in Chicago during Chicago Restaurant Week, a staple winter event in Chicago that gets everyone out of the house to enjoy the best dishes in Chicago. This annual event takes place in January and February, offering diners a chance to try out some of the city’s best restaurants at a discounted price. Over 250 restaurants participate in this event, each offering a special menu with prix-fixe options. Guests can enjoy a variety of cuisines, from Italian to Mexican to seafood.
See what’s new at the Chicago Cultural Center
Immerse yourself in culture for free at the Chicago Cultural Center. From art exhibits to live performances, it’s a hub of creativity, warmth, and a cool hangout during the winter months. The Chicago Cultural Center is a historic building in downtown Chicago, that offers a variety of free cultural events throughout the year. Visitors can enjoy art exhibits, live music performances, lectures, and more.
Volunteer for a grassroots organization
Winter is a great time to give back to your community by volunteering for a grassroots organization. From soup kitchens to animal shelters, many organizations could use your help during the colder months. Volunteering is a great way to meet new people, learn new skills, and make a difference in the lives of others. There are many ways to give back in Chicago, see some of our favorites here.
Escape to an indoor botanical garden under the glass
Explore the lush greenery and colorful flowers at an indoor conservatory in the city. Urban oases like Garfield Park Conservatory and The Lincoln Park Conservatory are home to thousands of plants from around the world, including rare and interesting species. Visitors can stroll through the various themed rooms each showcasing different plant varieties from around the globe.
Take on a new challenge or learn a new skill
Add some fun and excitement to your day by challenging yourself with a game room experience or learning a new skill in a class. Whether it’s mastering a new language, picking up a new instrument, or trying your hand at a new sport, there are plenty of opportunities to expand your horizons and discover new talents.
Learn something new and cool at a unique museum in Chicago
Take a break from the ordinary and immerse yourself in something truly unique by visiting one of Chicago’s many museums. From the American Writer’s Museum to theBusy Beaver Button Museum, there are plenty of options to choose from, each offering its fascinating exhibits and displays. Whether you’re interested in history, science, or art, you’re sure to find something that piques your curiosity and expands your mind.
Sip in style inside a rooftop igloo
Are you looking for a one-of-a-kind drinking experience? Look no further than an igloo bar! These cozy, enclosed structures are the perfect place to enjoy a drink with friends while staying warm and comfortable, even on the coldest of days. With their unique ambiance and stylish decor, igloo bars are the perfect place to relax, unwind, and enjoy some quality time with your favorite people.
