Chicago's Best Rooftop Bars

It’s all about the inventive cocktails, dark spirits and plush leather seats at Drumbar. Located in Gold Coast, this modern-day speakeasy perched atop the Raffaello Hotel has both indoor and outdoor seating and is an excellent place to nurse a cocktail and watch the sunset over Lake Michigan. Prop yourself up next to one of the outdoor firepits while you sip whiskey and scotch or try one of the four riffs on the classic old fashioned, swirled with gin, brandy or bourbon.

Fountainhead is a bar that revolves around beer and also boasts a seasonal rooftop garden. The cozy second-story terrace is rife with Chicagoans clutching steins of German ambers and Czech Pilsners. Along with beer, the menu is replete with bourbon, scotch, whiskey, wine and cocktails, which can be paired with snacks from the kitchen downstairs.

As the name suggests, the roof at The Garage Bar does whip up sandwiches: some teeming with crispy shrimp, others humble burgers elevated with a fried egg and bacon. Upstairs, the roof is decked out with comfy couches and green umbrellas, plus a changing list of 130 different beers, so even regulars can try something new. Plus, guests can play a handful of games like shuffleboard and darts.

Relatively new to the River North rooftop scene, Joy District fills up during happy hour with frozen drink-sipping dancers. The music is loud, the dancing is enthusiastic and the cucumber coolers are top-notch.

The swanky Virgin Hotel has an even swankier rooftop bar on the 26th floor. Its location in the heart of the Loop means the rooftop is surrounded by skyscrapers. Lounge furniture clad with green and blue pillows is scattered throughout the space, and there’s a changing selection of DJs pumping out dance music. Grab a glass of wine or a cocktail from the bar, then dunk pita chips into Mediterranean layered dip or pop back a couple of fried olives.

Cocktails are always the way to go at Cindy’s, a rooftop bar high above the Chicago Athletic Association Hotels. During the warmer months when the firepits are not in use, everyone spills onto the outdoor section – where there are unobstructed views of Millennium Park and The Bean – clutching highballs and piña coladas. The food menu is just as expansive as the bar itself, and on weekends brunch is served, with stacks of buttermilk pancakes and chilaquiles flying out of the kitchen.

The rooftop deck at the Godfrey Hotel may not be as high as the other rooftops scattered across the Windy City, but the sprawling space is outfitted with white booths, cabanas and tents. For those who don’t want bottle service, there are CBD cocktails, mojitos and margaritas, as well as beer and wine. During the Monday to Thursday 3–6pm happy hour, a handful of drinks are half price, and there are also discounted small plates, like black truffle fries and wagyu beef sliders.

The absolute best time to visit the Roof is in the middle of summer, when it buzzes with DJs and special guests. After all, it’s located on the 27th floor of theWit hotel, meaning there are unparalleled views of the Chicago River and Cloud Gate. Drinks run the gamut from house spritzes to bottle service, rounded out by a Spanish-leaning food menu: gnaw at potato croquettes, chicken and chorizo paella or pear and goat’s cheese flatbread.

Gene’s holds a bit of a secret: this unassuming sausage market opens up its roof in the summer, corralling al fresco lovers to their picnic tables. Here, you can knock back beers on tap and wines from around the world, then move onto sausages and bratwurst prepped on an open wood grill, plump pierogi jammed with sauerkraut and sweet cabbage and mustard-flecked potato salad.

An outpost of the eponymous Brooklyn bar, the Chicago version flaunts its very own rooftop deck. The roof serves the same signature cocktails and beers as downstairs, and has its own shuffleboard court, too. When you get hungry, take a walk to the food truck parked downstairs.

California meets Chicago at Ballast Point, equipped with an on-site brewing room. Nearly 40 beers are available on tap – from fruity and spicy iterations to rich and malty ones – which should be consumed on the cavernous rooftop with space for over a hundred people. You can fill a growler to take away or stick around and nibble on doughy, salt-crusted pretzels.