Winter in Chicago isn’t for the faint of heart, but that’s exactly what makes it unforgettable. From snow-dusted skylines to cozy hidden gems, the Windy City turns the cold into something worth celebrating.

While Chicago’s summer months dazzle with sun-soaked days filled with waterfront activities, there are still plenty of amazing things to do when temperatures drop. From ice skating in the reflection of the iconic Cloud Gate to drinking in Chicago culture, the Windy City’s colder months are anything but dull.
Outdoor activities
When winter wraps Chicago in its frosty embrace, it becomes an urban playground for cold-weather enthusiasts. Whether you’re gliding across ice rinks beneath towering skyscrapers or tackling a unique winter sport, there’s no shortage of fun things to do outdoors during winter in Chicago.

Ice skating
Strapping on a pair of skates and hitting the ice is a quintessential Chicago winter experience. One of the most popular spots is the McCormick Tribune Ice Rink in Millennium Park. Glide in the heart of downtown, with the glittering city skyline towering above and Cloud Gate, better known as The Bean, reflecting the festive glow of winter lights.
Once you’ve mastered your spins — or stumbled your way around Millennium Park — head just half a mile east for a totally different skating experience. Twice the length of a standard rink, the Skating Ribbon invites you to enjoy an extended and scenic skate, winding through Maggie Daley Park’s wintery charm.
Polar Adventure Days
When winter blankets Chicago, the city doesn’t hibernate, it celebrates. Hosted by the Chicago Park District, Polar Adventure Days invites you to embrace the chilly season with various free, family-friendly activities.
Held at Big Marsh Park, this event transforms this natural space into a bustling winter wonderland. You can watch teams of huskies pulling sleds, enjoy guided hikes and engage in nature-inspired crafts. Live music, storytelling around a bonfire and enjoying a cup of hot cocoa add to the festive atmosphere.
Curling
Want to channel your inner Olympian without leaving downtown Chicago? Several venues offer curling experiences that combine this casual ice sport with socializing.
At Harry Caray’s Tavern on Navy Pier, the Lakefront Lodge offers a private curling rink, heated igloo and firepit overlooking Lake Michigan. For a rooftop experience, head to Gwen’s Winter Curl & Chill. This Art Deco-inspired rooftop at The Gwen Hotel lets you challenge friends to a game while sipping seasonal cocktails like boozy hot chocolate and spiced mulled wine.
Indoor activities
When the Chicago winter drives you indoors, the city offers a variety of engaging experiences that keep the cold at bay. From breathtaking views from skyscraper observatories to impressive cultural institutions, there’s no shortage of indoor adventures to enjoy in Chicago during winter.

Chicago experiences with a view
Chicago offers several ways to take in its iconic skyline and the sparkling expanse of Lake Michigan from above. Start at Skydeck Chicago, where you’ll enjoy panoramic vistas of the city. But the real thrill comes from The Ledge, a glass balcony that extends 4.3 feet out from the building, putting nothing but clear glass between you and the bustling streets 1,353 feet below.
For another perspective, head to the 360 CHICAGO Observation Deck. This spot provides an equally breathtaking experience, offering stunning views of the city and the lake. For adrenaline seekers, TILT takes things to the next level — literally. This innovative platform tilts outward over Michigan Avenue, giving you a heart-pounding view of the city from 1,000 feet in the air.
If you prefer your vistas with a touch of whimsy, the Centennial Wheel at Navy Pier provides an elevated experience with less of an edge. This nearly 200-foot-tall Ferris wheel offers year-round, climate-controlled gondolas, making it a comfortable option even on the chilliest winter days.
Pro tip: Consider grabbing a Chicago CityPASS to save money on the city’s most popular attractions. It bundles admission to multiple must-see spots at a discounted price.

Garfield Park Conservatory
Escape the winter chill by entering the lush, tropical environment of the Garfield Park Conservatory. As one of the largest and most stunning indoor conservatories in the world, it houses thousands of plant species across eight rooms, including the Palm House and Fern Room.
Shedd Aquarium
Dive into the aquatic wonders at Shedd Aquarium, home to over 32,000 marine animals. Marvel at the playful beluga whales, explore the vibrant coral reefs and engage with interactive exhibits that educate and inspire.
Visit a museum
When the winter winds bite, there’s no better place to warm up than one of Chicago’s world-class museums. From art and history to science and architecture, the city’s cultural institutions accommodate a range of interests.
- Du Sable Museum of African American History. Dedicated to the study and preservation of African American history and culture, the DuSable Museum offers compelling exhibits.
- Field Museum. Embark on a voyage of discovery at the Field Museum, where you can encounter SUE, the largest and most complete T. rex ever found.
- Art Institute of Chicago. Home to a vast collection of artworks spanning centuries.
Culinary comforts
Chicago’s winter chill provides the perfect excuse to explore its rich culinary scene. Whether you’re sipping a steamy latte, indulging in world-famous comfort foods or discovering the city’s latest dining gems, your taste buds won’t care if the snow is piling up outside.
Cozy up to a warm beverage
Escape the cold with a visit to the Starbucks Reserve Roastery on Michigan Avenue. As the world’s largest Starbucks, this multi-level space offers an immersive coffee experience, complete with exclusive blends and artisanal brewing methods.
Chocolate lovers won’t want to miss the Nutella Cafe. Sip an indulgent hot chocolate or nibble one of many Nutella-infused treats in a cozy setting that celebrates the beloved hazelnut spread.

Dine at local gems
Chicago’s dining scene is a tapestry of flavors, with restaurants that cater to every palate. Here are some of my favorites:
- The Albert. Located within Hotel EMC2, The Albert offers a contemporary dining experience that blends art and science, featuring globally inspired cuisine in a stylish atmosphere.
- Eden. Situated in Chicago’s Avondale neighborhood, Eden brings a taste of paradise to Chicago with seasonal flavors sourced from their on-site greenhouse and local purveyors.
- Lil’ Ba-Ba-Reeba! The iconic small plates at Lil’ Ba-Ba-Reeba! will whisk you away to Spain with the first bite.
- Siena Tavern. This modern Italian eatery offers a blend of authentic flavors and contemporary dishes from Top Chef Fabio Viviani.
- Summer House Santa Monica. Bringing the warmth and laid-back vibes of the West Coast, it’s perpetually sunny inside Summer House.
Enjoy perennial Chicago favorites
Chicago is a city that takes its food seriously, and its signature dishes are no exception. From indulgent comfort foods to crave-worthy snacks, these local favorites are a must try for anyone visiting the Windy City.
- Deep-dish pizza: Chicago’s legendary pie features a buttery, flaky crust piled high with layers of cheese and toppings.
- Chicago-style hot dog: A beef frank in a steamed poppy seed bun topped with yellow mustard, relish, onions, tomatoes, a pickle spear, sport peppers and a dash of celery salt.
- Italian beef sandwich: A sandwich loaded with thinly sliced, seasoned roast beef on a crusty Italian roll.
- Garrett Popcorn’s Chicago-style popcorn mix: A perfect harmony of sweet caramel and tangy cheddar popcorn, this addictive snack is a favorite among locals.
Where to stay in Chicago
When visiting Chicago, choosing accommodations that offer both comfort and proximity to the city’s top attractions can enhance your experience. Here are two excellent options to consider:
- theWit Chicago, a Hilton Hotel. Situated in the heart of the Loop, theWit offers a vibrant atmosphere with modern design elements. Its central location provides easy access to the Chicago Theater, State Street shopping and the Chicago Riverwalk.
- The Blackstone, an Autograph Collection Hotel. Located on Michigan Avenue, The Blackstone is a storied architectural icon offering modern amenities and sweeping views of Lake Michigan and Grant Park. Its prime location places you within walking distance of cultural landmarks such as the Art Institute of Chicago and Millennium Park.
Embracing the Windy City’s winter wonders
Winter in Chicago may be brisk, but the city’s energy never freezes. Whether you’re skating beneath towering skyscrapers, savoring iconic comfort foods or warming up with a skyline view, there’s no shortage of ways to make the most of the season. So bundle up and embrace the magic — Chicago knows how to do winter right.
Sage Scott was bitten by the travel bug as a preschooler when her family moved abroad for the first time. Now settled in America’s Heartland, Sage is a travel writer, world wanderer and photographer whose favorite color is golden hour. Follow her adventures at Everyday Wanderer.