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Chicago's 12 Best Rooftop Bars

By Anthony Todd in Food on Aug 2, 2017 6:37PM

J. Parker roof via

By Leigh Kunkel and Anthony Todd

Summer is in full swing, and that can mean only one thing: Plenty of high-altitude drinking. Chicago has a ton of awesome rooftop bars where you can sip a cocktail, relax in the sun and forget about the stresses of life for a few hours. Here are our favorites.

J. Parker
When you have a lake as pretty as ours, it’s hard to beat a bar that looks straight out over it. Located in Lincoln Park atop the Lincoln Hotel, it's one of the only high altitude rooftop bars that aren't located downtown, and that's one of the things that makes it an incredibly popular destination. Lines stretch all the way down into the lobby on weekends, and our only successful technique for getting in involves showing up after the Green City Market, ten minutes before the place opens. Settle in, grab a snack and a Southern Belle, with bourbon, black tea, and peach, and remind yourself why you put yourself through the winters here.

La Josie
A relative newcomer to the Fulton Market District, the decor at La Josie is highlighted by understated neon (is that possible?) and a warm, neutral color scheme, all of designed to make the Jalisco-focused food and drink menu pop (Jalisco is a state of Mexico). There are three bars in the split-level eatery, culminating in a 50-seat rooftop patio. Float above the Randolph Street crowds, sipping on a perfectly made margarita, and be grateful that Jalisco has been kind enough to share.

The Garden at Celeste. Photo via Facebook

Garden at Celeste
For a quieter, more elegant evening, the Garden at Celeste is a small slice of urban River North, seen from an uncommon angle. Nestled amongst the vines and exposed brick, diners and drinkers can perch on Victorian wrought-iron furniture, admire antique bird cages and sip thoughtful, refined drinks.

Cliche though it may be, unpredictable weather is a fact of life in Chicago. But now it doesn’t have to stop you from enjoying the rooftop of the Kimpton Grey Hotel, rain or shine: Boleo, its Argentinian- and Peruvian-inspired bar, has a retractable glass roof. The cocktail list is just as exciting as the view, featuring a wide array of piscos, fernets, and other amari.

A rooftop doesn’t have to have a skyline view to be stunning. The cozy, intimate space above Wicker Park’s Taxim is surrounded by warm brick and glowing string lights, making it the perfect setting to sip a glass from their wide selection of under-the-radar Greek wines. There’s also a fascinating drink list called “Cocktails of the Greek Resistance,” featuring Greek spirits like raki and names like “Oligarchy’s Demise.”

Joy District
Admit it: sometimes “rooftop bar” actually means “outdoor club.” Nothing wrong with that, and it’s exactly what you’ll find at River North’s new Joy District. The eclectic mix of beautifully patterned tiles, industrial lighting, and lounge-style seating, combined with dancing and a cocktail list that’s half classics, half “basics” (looking at you, Pamatini), all add up to a night that you won’t remember until you check your Instagram feed the next morning.

Sausages at Gene's Rooftop. Photo by Anthony Todd.

Rooftop at Gene’s Sausage Shop
Residents of Lincoln Square practically live at Gene's during the summer, and it's not hard to see why. Located above the venerable German/Polish grocery store that boasts more types of canned pickled cabbage than any other place on earth, this low-key rooftop is filled with picnic tables, giant umbrellas and the smell of sausages on the grill. They've got a small draft program that's usually about half German and half American craft, a great food menu (get a giant grilled pretzel) and a kid-friendly atmosphere. But don't forget: It's the only bar on this list that's cash only.

Streeterville Social
This rooftop is huge. So huge, in fact, that when you're on it, you don't feel like you're on a roof; it's more like the entire rest of the city is somehow in the basement. Attached to the Loews Hotel in Streeterville, Streeterville Social is the largest rooftop bar/restaurant/lounge in the city. It's got a full food menu, cocktails and a "game lawn." Check out their frozen drink selection--on a hot day, what could be better than a real piƱa colada?

OK, GreenRiver isn't technically a "rooftop." But this bar/restaurant, located on the 18th floor, is actually higher up than most of the rooftop bars on this list, and has an expansive wrap-around balcony that's perfect for after-work relaxation. Unlike many rooftops, which sacrifice drink quality for volume and quaffability, GreenRiver boasts one of the top cocktail lists in the entire city, and it's all available outside.

With a name that means “hidden rooftop” in Japanese, you know you’re off to a good start. Perched on the top floor of the Conrad, the decor is sleek and understated and the menu heavy on the sake. The cocktail menu comprises mainly twists on classic cocktails, meant to go down easy while taking in a perfect skyline view. Don’t forget to check out the beer list, which features Japanese offerings beyond the ubiquitous Sapporo.

The interior of Cindy's. Photo via Facebook.

This rooftop bar atop the Chicago Athletic Association hotel boasts a stunning cocktail menu, a gorgeous design (you'll swear that the antique-looking girders have been there for 100 years, even though they were just built) and a view of Millennium Park unmatched by any other bar in Chicago. And since they’re open for lunch (and brunch on weekends), you can avoid the madding crowds in the evening and have the view all to yourself.

Another neighborhood rooftop, this Ravenswood bar known for its expansive beer and whiskey selection boasts one of the chillest rooftops in town. It's sunny, it's got its only small food menu with fun snacks like lobster deviled eggs, and there is literally no other rooftop bar in Chicago with a selection of drinks as good as this one.

The Terrace at Trump. Photo via Facebook

Terrace at Trump
Whatever you might think of the man whose name is spelled out in giant letters on the side of the building, Terrace at Trump is one of the most breathtaking spots in the city. Located on the 16th floor, with a view overlooking the Wrigley building and the Chicago River, the Terrace's grass-filled expanse (complete with tiny little bridges to perch on) is the definition of rooftop glamour. So the drinks are overpriced; you're not really paying for the booze.