Chilling in Chi-Town This Winter? Try These 10 Adventurous Cold Weather Activities in Chicago! CheapOair Staff December 21, 2021 Chicago, Destinations, Top US Destinations An average of three to four feet of snow blankets Chicago every year, so the Windy City has mastered how to have fun with winter weather. Whether you like the brisk outdoors or prefer to burrow indoors, Chicago provides a variety of fun outlets for all ages and interests. The next time you plan on making a trip to the Midwest, check out these adventurous winter activities in Chicago! Experience Winter Wonderfest on the Pier [Above image “20181212_131438” by Patrick Pelletier on Flickr – licensed under CC BY-SA 2.0]Every year, the Navy Pier hosts their very own Winter Wonderfest, with tons of twinkling lights and winter decor that sparkle against Lake Michigan. Year-round, Navy Pier has a carnival, an arcade of shops and restaurants, and a favorite lakefront spot for locals and tourists. If you have cheap domestic flights to Chicago for New Year’s Eve, there’s the New Year’s gala held in the Navy Pier Grand Ballroom followed by midnight fireworks over the lake. You won’t get a prettier, more spectacular view of the new year’s arrival anywhere else. Ice Skate By the Bean [Image above “Bean” by Michaela Pereckas on Flickr – licensed under CC by 2.0]C’mon, you have to try this — even if you’ve never laced up ice skates before. The rink at Millennium Park is now open, so rent some skates, grab a friend’s hand, and take a twirl or two on the ice. It’s a great way to get a little exercise. Plus, you’re skating right by one of the city’s masterpiece sculptures, “Cloud Gate” or what is more affectionately referred to as “the Bean.” Designed by Anish Kapoor and opened in 2006, the Bean has become one of the city’s hottest tourist attractions. Take in one of the best views of the Bean by gliding across the rink. Enjoy A Bird’s Eye View [Above image “The Hancock Observatory #16” by hibino on Flickr – licensed under CC by 2.0]Forget lines at the Sears Tower. Head to the John Hancock Observatory, and soak in the sky-high vistas from the city of Chicago below to the stretch of Lake Michigan ahead. And, on a really clear day, you can even see views of Wisconsin, Michigan, and Indiana. If you’re traveling with kids, Santa Claus sometimes keeps warm up in the Observatory before he fires up the sleigh on December 24, and he’s even willing to pose for selfies for good little girls and boys. Go Snowshoeing on Northerly Island If you’re looking for more outdoorsy winter activities in Chicago, lean into the snowshoeing opportunities at Northerly Island. This man-made peninsula situated on Lake Michigan is located just to the east of Soldier Field, providing a convenient escape from the hustle and bustle of the city. Get up close and personal with a bevy of wildlife and winter birds in their natural habitat as you trek through the snow. You’ll also be rewarded with stunning views of the Downtown Chicago skyline. The annual Polar Adventure Days is a free event that’s fun for the whole family, featuring arts and crafts, Siberian huskies encounters, and more. Related: 5 Kid-Friendly Attractions That Are a Must for Any Family Trip to Chicago Forget Deep Dish Pizza [Image above “Awesome vegan burgers at The Chicago Diner” by Beth Granter on Flickr – licensed under CC BY-SA 2.0]There’s far more to the Chicago food scene than the classic deep-dish pizza, which requires a knife, fork, and a lot of patience. A favorite Chicago dining spot that’s gained nationwide praise is Chicago Diner, one of the country’s first all-vegetarian diners and has been around for over 30 years. Whether you’re a die-hard carnivore or a true-blue vegan, Chicago Diner’s healthy comfort food hits the spot. You won’t taste better sweet potato fries, lentil-mushroom loaf or barbecue, or burgers anywhere else. This place converts people because it’s that good. Step Back in Time Chicago’s contribution to American music is indelible, and Reggie’s Rock Club is a brick-and-mortar valentine to all kinds of music. Located on South State Street, Reggie’s includes a huge vintage record store, a club featuring local talent, and a bar and grill. Reggie’s is a great place to cocoon on a winter’s day. Enjoy live music, greasy food, and find some really unique and classic records, as well as old issues of rock-n-roll magazines. Looking for Eartha Kitt’s 1953 classic “Santa Baby?” Reggie’s might have that. Sled Down Soldier Field While there’s no shortage of sledding options in and around Chi-Town, the Soldier’s Field Sledding Hill definitely takes the cake. The 33-foot slope delivers a host of thrills and chills as you fly down the hill on your sled. The city park service keeps the snow machine running all season long, ensuring that there’s always plenty of snow for you to enjoy. Before you take off down the hill, be sure to gaze at the panoramic view of Lake Michigan from the top of the hill. After you’re done with your sledding adventure, be sure to grab a bite to eat at one of the many nearby restaurants so that you can warm your toes and fill your belly up with some comfort food. Watch Digital Art at Art on theMART Art enthusiasts will appreciate the nightly showing of the digital art projections at the popular Art on theMART. Known as the largest permanent digital art projection on the planet, the show delivers contemporary artwork across a 2.5-acre river facade located at theMART. The 30-minute shows are projected twice nightly at The Merchandise Mart. You can watch the show from a variety of locations, including along the jetty of the Chicago Riverwalk or on Wacker Drive between Franklin Street and Wells Street. The free show is the perfect way to immerse yourself in the vibrant arts scene of Chicago. Try Curling on the Rooftop of the Gwen Hotel Haven’t tried curling yet? Now is your chance. Participants of this unique winter sport slide stones across a large sheet of ice aiming for a specific target. If you want to try your hand at curling, head up to the fifth floor of the Gwen Hotel to visit the rooftop and its iceless curling rink. Guests are invited to try this winter sport while cozying up with a warm cocktail. You’ll love the welcoming winter vibe of the terrace, featuring fire pits and loads of food and drink options. As a bonus, you’ll be treated to an amazing view of the Downtown skyline and the beauty of the city during winter. Enjoy the Warm Temperatures at the Garfield Park Conservatory Chicago may have the reputation for getting bitterly cold during the winter months, but there’s one place that’s always warm and cozy. The Garfield Park Conservatory is distinguished for being one of the largest botanical conservatories in the nation. The conservatory is home to thousands of unique plant species hailing from all over the world. All of these plants reside within the eight indoor gardens of the conservatory. With two acres of greenhouse space, there’s plenty of room to roam and enjoy the lush gardens and the warm and moist, tropical climate within the dome. What winter activities in Chicago have you tried? Tell us all about them in the comments below!