Winter in Chicago is cold, crisp, and completely unforgettable. Skaters glide beneath the city’s glittering skyline, snow-dusted streets lead to cozy cafés, and world-class museums offer a warm escape from the chill. Whether you’re bundling up for outdoor adventures or savoring the season from the comfort of a rooftop lounge, the Windy City knows how to make winter magical.
Chicago’s summer months may steal the spotlight, but the city doesn’t slow down when the temperature drops. Instead, it comes alive in a whole new way — twinkling lights reflect off frozen fountains, deep-dish pizza tastes even better after a chilly stroll down Michigan Avenue, and the city’s cultural gems provide the perfect indoor retreat.
From ice skating at Millennium Park to exploring the city’s renowned museums, winter in Chicago offers plenty of reasons to embrace the season. So layer up, grab a hot drink, and discover why this cold winter wonderland is one of the best places to be when the snow starts to fall.
Have You Visited Chicago in the Winter?
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Outdoor Activities
When winter weather sweeps through Chicago, the city 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. The city is home to several ice skating rinks that cater to both novices and seasoned skaters.
One of the most popular spots is the McCormick Tribune Ice Rink in Millennium Park. Located at 55 N. Michigan Ave, this iconic rink offers skaters a chance to glide in the heart of downtown, with the glittering city skyline towering above and Cloud Gate reflecting the festive glow of winter lights. If you ask me, this experience alone makes Chicago one of the most romantic Midwest getaways! The rink typically operates from mid-November through mid-March, weather permitting, and attracts over 100,000 skaters annually. Admission is free for those who bring their own skates, while skate rentals are available for a nominal fee.
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 traditional rink, the Skating Ribbon winds through Maggie Daley Park’s snowy landscape, offering a scenic, one-of-a-kind glide.
Ice Fishing
When Chicago freezes over, a few nearby spots turn into icy havens for winter anglers. Designated waterbodies in the Forest Preserves of Cook County, like Busse Reservoir and Beck Lake, offer accessible options for ice fishing enthusiasts without straying far from the city.
Conditions aren’t actively monitored by the Forest Preserves, so be sure to check for at least four inches of solid ice. New to the sport? Local guides and services like the Chicago Fishing School provide equipment, tips, and know-how to ensure a successful day on the ice. Don’t forget your Illinois fishing license, layer up, and let someone know where you’ll be. With the right prep, ice fishing is a peaceful, close-to-home way to enjoy Chicago’s winter beauty.
Polar Adventure Days
When winter blankets Chicago, the city doesn’t hibernate—it celebrates. Hosted by the Chicago Park District, Polar Adventure Days invite you to get outside and embrace the season with free, family-friendly fun.
Held at Big Marsh Park, this event transforms the space into a bustling winter wonderland. You can watch sled dogs in action, take guided nature hikes, and try your hand at seasonal crafts. Live music, storytelling around a bonfire, and steaming cups of hot cocoa make it a must for winter lovers of all ages.
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 features a private curling rink, heated igloo, and firepit overlooking Lake Michigan. For a rooftop experience, head to Gwen’s Winter Curl & Chill, where you can challenge friends to a match while sipping seasonal cocktails like boozy hot chocolate and spiced mulled wine.
Indoor Activities
When the cold winter air pushes you indoors, Chicago offers a plethora 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 during winter in Chicago.
Chicago Experiences with a View
Chicago offers several ways to take in its iconic skyline and the sparkling expanse of Lake Michigan from above. For the best views, start at Skydeck Chicago, on the 103rd floor of Willis Tower. Here, you’ll enjoy panoramic vistas of the city and, if you’re brave enough, step onto The Ledge—a glass balcony extending 4.3 feet from the building, leaving nothing but clear glass between you and the bustling streets 1,353 feet below.
For a different angle, head to the 360 CHICAGO Observation Deck on the 94th floor of the John Hancock Center. With sweeping views of the city and Lake Michigan, this spot is a must-visit. Feeling daring? Try TILT, an innovative platform that tilts outward over Michigan Avenue, giving you a heart-pounding look at the city from 1,000 feet in the air.
Prefer your high-altitude experience with a little less adrenaline? The Centennial Wheel at Navy Pier offers a gentler ride with year-round, climate-controlled gondolas, making it a cozy way to take in Chicago’s winter beauty.
Sage Advice: Consider grabbing a Chicago CityPASS to save money on the city’s most popular attractions, including Skydeck Chicago and 360 CHICAGO. It bundles admission to multiple must-see spots at a discounted price, making it a great deal for sightseeing-packed trips.
Garfield Park Conservatory
Escape the winter chill by stepping into the lush, tropical environment of the Garfield Park Conservatory. One of the largest and most impressive indoor conservatories in the world, it houses thousands of plant species across eight rooms, including the towering palms of the Palm House and the serene beauty of the Fern Room.
Shedd Aquarium
For an underwater escape, Shedd Aquarium is home to over 32,000 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 galleries and history to science and architecture, the city’s cultural institutions offer something for every interest.
- Du Sable Museum of African American History. Dedicated to the study and preservation of African American history and culture, the DuSable Museum features compelling exhibits on the contributions and experiences of African Americans.
- 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, explore ancient Egyptian tombs, and learn about cultures from around the world.
- Art Institute of Chicago. Home to a vast collection of artworks spanning centuries, the Art Institute boasts masterpieces like Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.”
- Chicago Children’s Museum. Located at Navy Pier, the Chicago Children’s Museum offers interactive exhibits designed to spark creativity and learning in children.
- Chicago Architecture Center. While winter may put a damper on architectural boat tours, the Chicago Architecture Center provides an indoor exploration of the city’s renowned architectural heritage.
Culinary Comforts
Chicago’s winter chill provides the perfect excuse to explore its rich culinary scene, from cozy beverages to hearty local dishes. 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 Café. Indulge in a rich hot chocolate or other 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 offering 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, toppings, and a rich tomato sauce on top.
- Chicago-Style Hot Dog: A beef frank nestled in a steamed poppy seed bun and “dragged through the garden” with yellow mustard, bright green relish, onions, tomatoes, a pickle spear, sport peppers, and a dash of celery salt. Just don’t ask for ketchup!
- Italian Beef Sandwich: A Chicago original, this sandwich is loaded with thinly sliced, seasoned roast beef on a crusty Italian roll, often dipped in jus and topped with spicy giardiniera or sweet peppers.
- Garrett Popcorn’s Chicago 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:
- The Blackstone, Autograph Collection. 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, making it an ideal base for exploring the city’s rich arts scene.
- 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. Be sure to visit the rooftop lounge for a nightcap with breathtaking views.
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.
Portions of this article originally appeared on Food Drink Life.
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