Find cocktails, curling, cocoa flights for holiday dining fun

Winter in Chicago transforms the city into a sparkling playground of unique experiences, where cozy indulgence meets vibrant activity. Imagine sharing a gourmet meal inside a heated igloo with breathtaking skyline views watching snowflakes drift past city lights in a warm and toasty igloo; or having fun engaging in a friendly curling match on a rooftop rink; or savoring decadent cocoa flights brimming with rich, imaginative flavors. These quintessential Chicago winter activities combine the city’s love for innovation (thank you, COVID) and its ability to make even the coldest months feel warm and inviting.

From buzzing downtown venues to charming neighborhood spots, Chicago offers a winter wonderland of experiences that are as dynamic as the city itself.

Reflecting the creativity and resilience of local restaurant and bar owners, outdoor igloo dining has become a staple of Chicago’s culinary scene since the days of COVID. What began as a necessity has evolved into a beloved tradition that’s here to stay. Some venues have even taken it a step further, transforming open-air patios into massive snow globes by enclosing entire spaces in glass. Can you imagine anything more magical than admiring Chicago’s breathtaking skyline from inside a sparkling snow globe? Add to that a menu of craft beverages and unique activities, and you will have an unforgettable winter experience.

Curling and cocktails and cabanas, oh my!

Cabana and igloo dining in Chicago has become as iconic as deep-dish pizza or the sparkling lights of the Magnificent Mile during the holiday season. With countless options to choose from, standing out requires creativity—and many establishments across the city and suburbs have risen to the occasion with bold, unique offerings.

Upstairs at The Gwen – Winter Curl and Chill Rooftop Terrace

Perched on the fifth-floor rooftop terrace of The Gwen Hotel along Michigan Avenue, this winter wonderland features a synthetic ice curling lane and cozy fire tables to keep you warm between matches. Guests can enjoy craft cocktails and festive treats from a holiday-inspired menu. Reservations are essential, but the fun and festive atmosphere lasts all season long!

Lakefront Lodge at Harry Caray’s at Navy Pier

What’s better than curling on a rooftop terrace? Curling with a stunning lakefront view at Navy Pier. Harry Caray’s outdoor patio has been transformed into a cozy winter retreat, complete with a curling lane, firepits, and heated igloos for an unforgettable seasonal experience. Guests can enjoy craft cocktails and a specially curated holiday menu. Reservations are required for this lakeside winter wonderland.

Winter Garden at Chateau Carbide at Pendry Chicago

Located atop the iconic Carbide & Carbon building near the Loop, the Winter Garden is a picturesque retreat offering cozy chalets that seat up to six guests. Each chalet comes with its own private fireplace and extra blankets, keeping you warm while you enjoy chilled drinks. Their holiday menu features a selection of small bites and seasonal craft cocktails, served Thursday through Saturday from 5 p.m. to 11 p.m. The best part? No reservations are required to experience this charming rooftop getaway.

Kennedy Rooftop at theHyatt Place Chicago in Wicker Park

With stunning skyline views as your backdrop, relax in your private igloo, adorned with twinkling lights, for a warm and cozy evening. Step outside for some friendly competition on the curling lanes. Visit the link for details on packages and reservations.

Offshore Rooftop

Fun fact: The Guinness Book of World Records has recognized the Offshore Rooftop as the largest rooftop bar in the world! For the winter season, it has been transformed into the world’s largest snow globe. Encased in all-weather glass, guests can enjoy breathtaking, unobstructed views of Lake Michigan and the city skyline. From Dec. 6 through Jan. 31, step into the past with their “Retro Under the Mistletoe Pop-up,” where vintage Christmas decorations evoke nostalgic childhood memories. Enjoy craft and warm cocktails to celebrate the season. The fun doesn’t stop there, follow this link for a full list of winter happenings. If you’re lucky enough to be there during the Navy Pier winter fireworks, you’ll have the best seat in the city. Reservations are required

Holly Jolly: Curling and Cocktails atWhiskey Business

Cocktails, Mocktails, and Curling--Oh My! Until Dec. 28, Whiskey Business Bar in Wicker Park has transformed into the Holly Jolly Holiday Bar. Decked out with floor-to-ceiling Christmas lights, tinsel, and ornaments, guests can enjoy a festive menu of holiday-themed cocktails and mocktails. Tickets are required and can be purchased via the link provided. But the fun doesn’t stop there! Throughout the winter, the rooftop tent will be open, offering curling lanes, movie nights, Bears game day packages, brunch, and more.

Cocoa flights and beyond with the kids

Perfect for kids–and kids at heart–sampling rich and velvety hot chocolates in creative flavors or building the ultimate sundae piled high with toppings is the perfect way to treat the family to a little sweetness on a chilly day. These fun and delicious outings bring a sprinkle of magic to any day.

JoJo’s Shake Bar

With multiple locations across the city and suburbs, Jojo’s Shake Bar transforms into a festive Winter Wonderland. Each location is adorned with holiday decorations, specialty menus, and seasonal activities. The Naperville location goes all out by turning its rooftop outdoor seating into a heated Christmas treehouse. Be sure to try Rudolph’s Hot Chocolate Flight, featuring custom flavors like Toasted Marshmallow with a pink chocolate-dipped marshmallow, Double Chocolate Toasted Marshmallow with a double-chocolate-coated marshmallow, Salted Caramel Toasted Marshmallow with a chocolate-dipped marshmallow rolled in toffee bits, and Peppermint Toasted Marshmallow with a white snowflake-shaped marshmallow dusted in pink sugar. Here’s an insider tip: Bring your own Thermos, and Jojo’s will fill it with their signature hot cocoa for just $4.99 all winter long.

Katherine Anne Confections

At Katherine Anne Confections, everything is made fresh in-house using high-quality ingredients and a lot of passion. While their selection of treats and drinks is impressive, the drinking chocolate is truly magical. Instead of cocoa powder, they use shaved chocolate blended with warm milk, creating a rich, decadent cup of perfectly balanced, not-too-sweet chocolate. For the ultimate experience, try their cocoa flight, which lets you sample three unique flavors: Semisweet (58 percent), Bittersweet (72 percent), and Super Dark (85 percent); Salted Caramel made with Katherine Anne toffee chunks with a sprinkle of flaky sea salt, and Mexican Hot Chocolate spiced with their own custom blend of cinnamon, cayenne, habanero, and guajillo chiles. If you're stopping by for a sweet treat, you must experience  the cocoa flight. It truly is an adventure for your taste buds.

Creamery

While it may require a drive outside the city, the experience at The Creamery’s Homer Glen, Sandwich, and Manhattan, Ill., locations is well worth the trip. From November to March, you can enjoy their unique Creamery Igloo Experience, with two tempting options that will have you wanting to return for more. Both experiences take place in heated igloos that seat up to six people (lap babies are not included in the headcount). Starting at 5 p.m., every 15 minutes, the igloos light up with a holiday-themed light show set to festive tunes. Reservations are required, and they ask that you arrive 15 minutes early.

You can choose between the Hot Chocolate Bar Experience or the Sundae Bar Experience. The Hot Chocolate Bar includes six jumbo chocolate chip cookies, hot cocoa for six, an assortment of toppings, and two take-home pints of your favorite Creamery ice cream packed in an insulated bag. The Sundae Bar Experience offers two quarts of your favorite ice cream, six jumbo cookies, a variety of toppings, waffle cones and sundae cups, plus two pints of ice cream packed in an insulated bag for the journey home. For reservations and more details, follow this link. 

Winter in Chicago can be long. Whether you spend time with friends toasting craft cocktails, competing on the curling rink, indulging in decadent desserts or enjoying an intimate meal in a glowing igloo, these experiences can transform the chilly months into a time of magic and joy. So, embrace the magic of the winter and let Chicago’s winter wonders warm your heart and soul.