Chicago's Best Year Round Rooftop Bars

Does winter have you feeling blue? In dire need of a dose of Vitamin D and the illusion of warmer weather? Fortunately for you, Chicago has filled up nicely in recent years with a handful of rooftop terraces, bars and restaurants that are open year round. Of course, they are now enclosed so that you don’t freeze to death while sipping your cocktail, but with the views and the natural light still accounted for, it’s a breath of fresh winter air. Here’s where to dine and drink on rooftops this winter in Chicago.

Boleo; photo by Sarah Joyce


Raised: This massive low-flying rooftop bar and restaurant opened late last spring and has been red hot ever since. Including right now, when you could use that heat the most. It’s got a massive indoor space overlooking the Chicago River and the River North skyline, and it’s also not too high up, which is a nice option for those afraid of heights. Raised also raises the bar on food, which elevates American bar fare thanks to chef Daniel Perez. Items include deviled eggs with n’duja, kabocha squash fritters and crispy Brussels sprouts with apple-bourbon reduction. 

Up & Up: The newest addition to Chicago’s rooftop bar scene is Up & Up, perched atop Wicker Park’s brand new (and stunningly cool) Robey Hotel. Far enough from the downtown core, the 13th story cocktail nook sports glorious views regardless of whether or not the outdoor terrace is open. The indoor area for now is cozy and warm, outfitted with snug lounge chairs and sofas; great perches for sipping inventive and boozy libations like newfangled riffs on Old Fashioneds. 

The J. Parker: A perpetual crowd-pleaser in the warmer months, Lincoln Park’s J. Parker is now equally hip all year round thanks to the addition of a retractable glass roof. Wrapping around the expansive patio like an igloo dome, guests can still drink in the views of the park, the lake and the downtown skyline, all while drinking in the Boss cocktail, a warm winter tipple made with whiskey, spiced chocolate and whipped cream. Round it out with snacks like truffle frites, grilled cheese sandwiches and brownies. 
Cindy’s: No matter the time of day or year, the stunning atrium-like terrace atop the Chicago Athletic Association radiates warm vibes and chic ambience. That might explain why it’s always crazy packed. If the temperature isn’t too frigid, guests can take their cocktails out onto the open air terrace and sit by a roaring fireplace (the bar provides blankets, too!). Or just cozy up inside with a boozy hot chocolate and a shellfish platter and call it a night. 

Boleo: As if the glass roof-enclosed rooftop restaurant at the new Kimpton Gray Hotel wasn’t beautiful enough, the Latin American cuisine and inventive cocktails are sure to bolster that sense of exoticism and warmth. No matter the forecast, Boleo feels sunny and tropical, thanks to an abundance of green plants and lounge-like chairs, tables and banquettes. The menu is refreshing, too. Be sure and share some bracing ceviches, some tuna tataki anticuchos and some lobster tempura rolls. Don’t worry about sharing the cocktails, though. Those you’ll want to keep all for yourself.