10 Cozy Spots in Chicago to Experience the Best of the Winter Season
Sip cocktails by a crackling fireplace at a trendy lounge, check out the coffee-shop scene, admire world-class art at a museum and experience the warmth of a luxury spa.
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Chicago’s moniker may be the Windy City and yes, winters are very frigid in this Midwest metropolis that hugs Lake Michigan, but this is also the coziest season of the year. There’s no shortage of fun things to do, whether you’re partial to outdoor activities or would rather stay inside. Sip cocktails by a crackling fireplace at a trendy lounge, check out the coffee-shop scene, admire world-class art at a museum or experience the warmth of a luxury spa. For those that prefer indoor activities, many of the city’s rooftop bars are glass-enclosed, which capitalize on a skyline view at night while keeping things cozy. Outdoor events are equally festive and cozy; go ice skating, explore a traditional Christmas market and experience the annual Magnificent Mile Lights Festival on Nov. 23.
In recent Chicago winters, heavy snow and otherwise blustery, frigid cold weather haven’t hit the city until the New Year, so a visit in late November and into December can expect to be mild. This is also when you can dine under a larger-than-life Christmas tree in the Walnut Room at Macy’s on State Street, view the department store’s festive holiday window displays, or marvel at light displays after dark, including ZooLights at Lincoln Park Zoo and Lightscape at the Chicago Botanic Garden.
Pack a parka and warm outerwear, along with your coziest sweater, and get ready for a festive getaway in Chicago during its most underrated time of the year.
The Ultimate Guide to Winter in the Windy City
Cindy's Rooftop
- 12 S. Michigan Ave., Chicago, IL 60603
Park on Michigan Avenue, this glass-enclosed rooftop space is equipped for the winter months with fire pits on the South Terrace. A new après ski-inspired, hot cocktail pop-up through the end of February means you can sip cocktails such as spiced mulled wine, buttered rum, hot toddies and hot cocoa with Rémy Martin 1738 and vegan whipped cream, while taking in dreamy views of Lake Michigan and The Bean (also known as Cloud Gate).
Garfield Park Conservatory
- 300 N. Central Park Ave., Chicago, IL 60624
Acclaimed landscape designer Jens Jensen designed this conservatory between 1905 and 1907. Inside this West Side conservatory’s glass structures, the temperature spikes and turns humid, allowing you to shed a winter coat while surrounded by tropical foliage. At Palm House, its largest indoor garden at 65 feet tall, palm trees commune with plants and trees found in warm climates around the world. Desert House, home to cacti and succulents, is a veritable trip to the hot desert. Another bright spot during cold winter days is the Fern Room, featuring an indoor lagoon.
Christkindlmarket Chicago
- 50 W. Washington St., Chicago, IL 60602
Open in Daley Plaza between Nov. 22 and Dec. 24, this outdoor market’s vendors are tucked into candy-cane-striped huts modeled after those at a Christmas market in Nuremberg, Germany. Order glühwein in a souvenir ceramic boot mug or fill up a collective ceramic beer stein at this winter wonderland. Crafts sold at the outdoor market include ornaments for the holiday tree as well as nativity scenes and embroidered lace imported from Germany, and art from Slavic and Ukrainian artists. You can also sample German sweets and snacks, including currywurst, large baked pretzels, potato pancakes, leberkäse, schnitzel, gingerbread and German cookies.
Museum of Contemporary Art Chicago
- 220 E. Chicago Ave., Chicago, IL 60611
Designed by Josef Paul Kleihues, who relied on lots of aluminum as well as Indiana limestone, MCA is one of the world’s largest contemporary art museums. Through Dec. 1, an exhibit mentally transports visitors to a warmer climate (“Trade Windings: De-Lineating the American Tropics”), showcasing artists across various mediums as they narrate authentic stories about trade routes across the Atlantic during the 15th and 16th centuries. Insider tip—on Tuesdays, Illinois residents get free admission. Weekend brunch at the Chicago museum’s Marisol Restaurant & Bar features hot eats like beignets and house sausage along with typical breakfast entrees.
Chuan Spa at The Langham, Chicago
- 330 N. Wabash Ave., Chicago, IL 60611
Within an architectural marvel designed by Ludwig Mies van der Rohe, where 13 floors are dedicated to the hotel, this Asian-influenced spa is inspired by five elements: metal, wood, water, fire and earth. Two treatments on the menu immediately invite warmth: Chuan Tao of Detox, a warm marine-algae wrap and acupressure massage; and Hot Himalayan Salt Stone Massage, where these warmed stones alleviate body aches, stress and anxiety, while balancing one’s chakras.
Maggie Daley Park Ice Skating Ribbon
- 337 E. Randolph St., Chicago, IL 60601
Work up a light sweat at this outdoor ice skating rink in the Loop neighborhood in Millennium Park. Instead of a square or a circle, the rink is shaped like a ribbon. Skate rentals are available in both children and adult sizes. At night, downtown Chicago’s skyline surrounds the rink, adding instant glow and glitter, and it’s easy to reach. Located between Columbus Drive and Lake Shore Drive, just look for the Frank Gehry-designed Jay Pritzker Pavilion, as its sheets of metal shine thanks to colored back-lighting.
Boleo
- 122 W. Monroe St., Chicago, IL 60603
Cuisine at this enclosed rooftop at Kimpton Gray Hotel skews towards Latin American, including ceviche, empanadas, braised octopus and yucca fries. From a pisco sour to a guava-and-mezcal cocktail, the drinks are equally on par with what you’d crave in a warmer climate. The spacious bar’s lush plantscape also channels the tropics, and there are lots of sofas for lounging, in addition to dining tables and bar seating.
Geja's Cafe
- 340 W. Armitage Ave., Chicago, IL 60614
With its cozy booths and timeless interiors, Geja’s Café has long been heralded as a great date night spot year-round. This fondue-focused restaurant celebrates its 59th year in 2025, and is especially enticing during the winter months. Go all in with both the Swiss gruyère cheese and the chocolate fondue service, and cold-water lobster tail and beef tenderloin for dinner, or drop in for à la carte fondue only. Some evenings, live flamenco and classical guitar music fill the restaurant, making it feel even more intimate. Flutes and bottles of Champagne are included on the lengthy wine list, along with hearty reds and crisp whites
The Gwen Hotel
- 521 N. Rush St., Chicago, IL 60611
After Nov. 23, this Mag Mile hotel’s rooftop terrace transforms into Winter Curl & Chill for the holiday season. Curling, which is a winter sport where you slide stones on ice, is the anchor winter activity, but you can also kick back and warm up with boozy hot cocoa in a mug. These seasonal creations include tipsy teas, cocktails flaunting burnt marshmallows bobbing on top and eggnog flights, perfect to enjoy while cuddled up in a fuzzy throw in front of the fire. Sweet treats are also available as pairings.
Mindy's Bakery
- 1623 N. Milwaukee Ave., Chicago, IL 60647
Celebrated pastry chef Mindy Segal, who was named Outstanding Pastry Chef by the James Beard Foundation, owns this Wicker Park bakery, where the hot chocolate is more haute than it is run of the mill. A touch of dark chocolate is added to milk chocolate for a deeply layered effect and there’s house-made marshmallow on top. While not a full-service restaurant, there are a few stools by the window to sit and savor this hot beverage.
