Winter in Chicago: How to Enjoy It Like a Local

Winters in Chicago are the stuff of history books. When the season descends, the city undergoes a magical transformation — Lake Michigan freezes into a sheet of ice, snow dusts the skyscrapers, and the streets grow calm and quiet.

For many, this sudden change might sound harsh or even unwelcoming, but locals know that winter here has its own kind of magic. With the right mindset, gear, and itinerary, anyone can fall in love with Chicago’s winter season. Let’s see how to enjoy winter like a local with this list of the best winter attractions in Chicago.

Ice skating in Chicago is a year-round favorite, but its iconic outdoor rinks truly shine during the winter months. The most popular is the McCormick Tribune Ice Rink, located in Millennium Park right along Michigan Avenue. Skaters enjoy gliding beneath Chicago’s skyline, with the Art Institute of Chicago and the Cultural Mile as a backdrop. Admission is free — you only pay for skate rentals.

Another great option is Maggie Daley Park, which offers an alpine-inspired skating ribbon that winds through snow-covered scenery, adding an adventurous twist to your skating experience.

Think boating in winter is impossible? Think again! The Chicago River Cruise offers an unforgettable experience with its hot tub boat rides, letting you relax in warm water while floating through the icy beauty of the city. It’s especially romantic during winter nights when snowflakes fall over the river and the skyline sparkles in the frost.

Nothing captures the spirit of winter like a traditional German Christmas Market, and Chicago’s Christkindlmarket is among the best in the country. The scent of roasted nuts, mulled wine, and hot chocolate fills the air while vendors sell handcrafted ornaments, festive decorations, and unique gifts. It’s a perfect spot to shop, sip, and soak in the holiday cheer.

The Centennial Wheel at Navy Pier offers breathtaking panoramic views of the frozen Lake Michigan and the snow-covered city skyline from nearly 200 feet in the air. Don’t worry — the gondolas are fully temperature-controlled, so you can stay cozy while enjoying the view. Just bundle up while waiting in line!

Chicago’s Holiday Tree Lighting Ceremony officially kicks off the festive season and takes place each year before Thanksgiving at Millennium Park. The event is free and open to all. A charming tradition accompanies it — the tree is always selected from a local resident’s donation and must stand at least 55 feet tall, symbolizing the community spirit of the city.

When the snow falls, Chicago’s parks turn into serene winter wonderlands. Locals love walking through these frosty landscapes, breathing in crisp air, and listening to the crunch of snow underfoot. Some of the best winter spots include Northerly Island Park and Big Marsh Park, where you can admire winter wildlife and the quiet beauty of frozen nature.

One of Chicago’s most dazzling winter events, the Magnificent Mile Lights Festival features live music, parades, shopping deals, and over a million twinkling lights. Held the weekend before Thanksgiving, it’s one of the city’s most beloved traditions. Visitors should explore Pioneer Court, which hosts family-friendly activities and a festive holiday market.

No Chicago winter is complete without indulging in a classic deep-dish pizza. Thick, cheesy, and baked to perfection, this comforting dish is the ultimate way to warm up on a cold day. The gooey cheese and tangy tomato sauce layered over the buttery crust deliver a burst of flavor and warmth with every bite — pure comfort food, Chicago-style.

Stay in the heart of Chicago this winter — where comfort meets skyline views and every cozy stay puts you steps away from the city’s top attractions with these hotels:

8.4 Very good

Chicago Athletic Association part of Hyatt

12 South Michigan Avenue Chicago, us

8.1 Very good

Radisson Blu Aqua Hotel Chicago

221 North Columbus Drive Chicago, us

8.3 Very good

Fairmont Chicago Millennium Park

200 North Columbus Chicago, us