Winter is almost here (we know, ugh), but that doesn’t mean you have to miss out on enjoying the Chicago skyline from a higher vantage point. Rooftop season can continue year-round, thanks to the winter rooftop bars in Chicago that offer warmth and stunning views.
With options like igloos, ski lodges, fire pits, and more, there are plenty of unique winter rooftop bars in Chicago that promise a memorable evening during the cold months. Here are some of the best winter rooftops in Chicago worth visiting.
Château Carbide
Chateau Carbide’s indoor-outdoor lounge will be completely transformed into a Winter Garden, featuring luxurious private chalets scattered across the rooftop. Each chalet will be adorned with relaxing fireplaces, warm blankets, and seating for up to six guests. The winter-inspired menu includes small bites and seasonal cocktails that are perfect for starting or ending your night.
Address: 230 N Michigan Ave, Chicago, IL 60601
Cindy Rooftop
Visit Cindy’s Hot Cocktail Pop-Up, where you can enjoy winter flavors through a modern and inclusive lens. This pop-up features a welcoming rooftop winter retreat in Chicago, perfect for relaxing with seasonal drinks while enjoying scenic city views and a cozy atmosphere. The team has crafted comforting cocktails that cater to everyone, including vegans and those who are dairy-free. Here’s a sampling of what guests can enjoy: Hot Cocoa, Buttered Rum, Hot Toddy, and Mulled Wine.
Address: 12 S Michigan Ave, Chicago, IL 60603
The Godfrey Hotel’s Rooftop
One of Chicago’s best winter rooftop bars is at the Godfrey Hotel—it’s an actual winter wonderland. The fourth-floor terrace seamlessly transitions into an astounding outdoor oasis with scintillating lights, snow, and igloos. Grab a drink and gaze out the rooftop, or cozy up in one of the many heated dome igloos for a special winter wonderland night..
Address: 127 W Huron St, Chicago, IL 60654
Sifr
Sifr boasts the largest rooftop in River North and is now open year-round, so it deserves a spot on your list of places to visit. Not only does Sifr offer a unique culinary experience paired with exceptional dining, but it also provides breathtaking views of the city across the changing seasons. The spot is perfect for any occasion, featuring an enclosed rooftop equipped with multiple heaters to ensure a comfortable dining experience for all guests.
The menu showcases hearty dishes and cocktails that celebrate the spices and flavors of the Middle Eastern diaspora. It invites guests of all tastes to savor the rich flavors of the region in the dining room, bar, and new heated rooftop space.
Address: 660 N Orleans St, Chicago, IL 60654
The Gwen Hotel’s Rooftop
If you’re looking for something different, The Gwen Hotel’s rooftop has the answers. While you won’t find lavish igloos here, you’ll instead be able to enjoy the hotel’s annual Curling and cocktails experience. During winter, the hotel kits out its winter rooftop in Chicago with an outdoor curling rink high in the sky.
Curling sessions come with complimentary cocktails, meaning you can sip away on your favorite tipple while battling your buddies on the state-of-the-art curling rink—of course, this makes it one of the best winter rooftop bars in Chicago.
Address: 521 N Rush St, Chicago, IL 60611
London House Chicago’s Rooftop
Recently named one of the best hotels on the planet, LondonHouse also offers an elegant tri-level winter rooftop bar in Chicago. Renowned for having some of the best views in Chicago, the luxury hotel frequently festoons its rooftop for varying seasonal soirees. Now returning for its fourth year, the festive “Rudolph’s Rooftop” experience offers whimsical décor, rentable outdoor igloos, and celebratory cocktails at a sensational seasonal setup on one of Chicago’s most iconic rooftops.
Address: 85 E Wacker Dr, Chicago, IL 60601
Whiskey Business’s Rooftop
On a 3000-square-foot Wicker Park rooftop high above 1367 N Milwaukee Avenue, Whiskey Business has created a multifunctional space to run events throughout winter. One of the best winter rooftop bars in Chicago, Whiskey Business has rooftop movie nights,weekend brunches, a curling rink and a sports bar Chicago Bears gameday packages offer something for everybody. This year, the bar has also pitched an enormous glowing tent on its rooftop so that guests can stay warm and cozy while enjoying a few drinks.
Address:1367 N Milwaukee Ave, Chicago, IL 60622
The VU Rooftop
While you won’t find domes, igloos, or anything above you at VU, there are safe large firepits situated all around the rooftop so that you can stay toasty warm while taking in unparalleled views of the lake, South Loop Chicago, Museum Campus, and often some sublime sunset spectacles.
The 13,000-square-foot South Loop space is home to three different bars and two patios where you can enjoy top-notch cocktails and bites. Note that this ritzy rooftop VU follows a classy and fun dress code, so make sure to pull out your best outfits for the occasion and leave your casual wear at home.
Address: 133 E Cermak Rd, Chicago, IL 60616
The Kennedy Rooftop
The Kennedy Rooftop is Wicker Park’s very own urban chic hideout. The interior, food, and drink options are all designed to accentuate the city’s modern, trendy, and diverse fabric. Panoramic views of Chicago’s iconic skyline and a comfortable layout make it a phenomenal rooftop option, and luckily, its igloos have returned for another Chicago winter.
Like the Gwen Hotel, the Kennedy Rooftop is also home to a curling lane. This means you can enjoy a classy evening on the plush rooftop while having a bit of competitive fun to keep you warm.
Address: 1551 W North Ave Ashland, Chicago, IL 60622
Offshore Rooftop
The Offshore Rooftop is the largest rooftop deck in the country and is consistently recognized as one of the best places to enjoy a drink with a view. Its panoramic views of Lake Michigan and the city skyline are unmatched. While most rooftops are among the skyline and thus offer views over the city, the Offshore Rooftop allows you to gaze at Chicago’s famous skyline.
Address: 1000 E Grand Ave, Chicago, IL 60611
The J. Parker Rooftop
While Chicago is home to an array of astounding rooftops, few offer 360-degree views of the city. Up at Hotel Lincoln’s J. Parker Rooftop, however, you will find just that in addition to front-row seats of Lake Michigan and Lincoln Park and its stunning winter spectacle.
With indoor and outdoor seating, a glass retractable roof, and floor-to-ceiling windows, plenty of options exist to sit and enjoy the scintillating views. Seasonal drinks include various forms of hot toddies, mulled wines, and ciders.
Address: 1816 N Clark St, Chicago, IL 60614
Joy District’s Rooftop
Few rooftops can compete with the astounding setup at Joy District. One of the best winter rooftop bars in Chicago—Joy district has sparkling lights, comfortable patterned couches, and impeccable views of Chicago’s skyline guarantee a memorable night, but it’s the magic of vibrant murals and cascading greenery that truly makes Joy District’s rooftop a unique space.
Address: 112 W Hubbard St, Chicago, IL 60654