What to Do in Chicago This Winter

There is plenty of outdoor fun to be had if you can brave the cold in Chicago, and if the weather outside is too frightful, we have cozy spots at which to defrost, too, with delicious, heartwarming food.

Ice skating at Millennium Park is iconic, and admission is free, with skates available to rent. Just north of the park’s Pritzker Pavilion you’ll find Maggie Daley Park, where each winter a track is transformed into a quarter-mile ice skating ribbon, which skaters can glide along while eyeing The Windy City’s iconic skyline.

For an unexpected twist on outdoor winter sports, consider curling. Local gastropub Kaiser Tiger gives a nod to the sport each season when it unveils three ice curling rinks in their beer garden.

For a sporty winter adventure that doesn’t involve leaving the city (or a heated space), channel your inner climber and scale mountains indoors at Brooklyn Boulders or First Ascent.

For some rooftop fun, head to Joy District just down the street and cozy up around the faux fire pit in a heated igloo. The hip restaurant and cocktail bar will serve themed cocktails in ornaments and snowball fishbowls, and igloos are available for groups of up to 12 people. The igloos are decorated in shades of white, light blue and silver, with string lights, ornaments, winter props and blankets.

Pair your winter-themed margarita with seasonal bites like cranberry brie crostini and honey ham sliders. For dessert, there’s a milk-and-cookies cart presented tableside — decorate sugar cookies with frosting and sprinkles with a shot of RumChata.

For a kid-friendly treat, the thick, European-style sipping chocolate and hand-rolled truffles at Katherine Anne Confections in Logan Square or the bean-to-cup Mexican cacao hot chocolate at Rick Bayless’ XOCO in River North. Try your freshly ground hot chocolate Aztec-style, with chili and allspice.

If you’re looking to warm up with some shopping, there are several local favorites for everything from home decor to fashion and makeup. Jayson Home has been a favorite of the city’s top interior designers for years for their unique collection of one-of-a-kind vintage and antique items, from fine furniture to brocante curiosities, unearthed in far flung destinations from Europe to Morocco and India.

You could spend hours wandering the 20,000-square-foot converted warehouse. If you like cosmetics, you will love the immersive new Winky Lux store that just opened in the Shops at North Bridge, where you can have a midday dance party and play in a lemon-themed ball pit in addition to finding your perfect shade of lipstick.

For an aerial view of the city, take flight with Chicago Helicopter Experience. When it’s snowing, you’ll feel like you’re in a snow globe as you fly north over Chicago’s Museum Campus, spotting landmarks like Buckingham Fountain, Grant Park, Willis Tower and the Wrigley Building. There are both day and evening tours, and it’s a neat perspective after exploring the city by foot.

If you’d rather stay closer to land, plan a visit to Garfield Park Conservatory, where you can keep cozy while wandering through two acres of indoor plant displays, including the Fern Room, which offers glimpses of Chicago’s prehistoric plant life.

Hearth-inspired cooking is all the rage in Chicago these days, and what better way to warm up frozen fingers than with a hearty meal next to the fire? Request the chef’s counter at El Che Bar and you’ll be just a few feet away from the 12-foot hearth at this Argentine steakhouse. But every seat in the house has a view of the live-fire cooking, where everything from bone-in rib-eye with chimichurri sauce to empanadas and charred vegetables are prepared.

Etta is another great new restaurant specializing in wood-fired cooking. The rustic, fire-kissed food uses the best in Midwest produce, including crispy kalettes, and the Bubbling Shrimp seasoned with ginger, chili and smoked tomato are a must. Don’t skip the Neapolitan-inspired pizzas, either. You’ll be fighting over the last slice of the spicy guanciale pizza and cheesy wild mushroom pie topped with truffles. Just what you need to fuel your winter adventures.