The 9 Best Rooftop Bars In Chicago

By Anthony Todd in Food on Jun 6, 2016 2:46PM

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.

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J. Parker roof via http://www.jparkerchicago.com/

J. Parker

The J. Parker is unique amongst the bars on this list because of it's incredible lake views. 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. But with refreshing cocktails and snacks by Paul Virant, we can't be too mad that it's always packed.

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 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." Their drink menu features pre-batched (but still complex) cocktails, like the "Birkenstocks," a combo of Hennessy VS, Carpano Antica Sweet Vermouth, Cherry Herring and House-made Gingerbread Dream Rooibos Syrup, and they've also got a large selection of large format bottled cocktails for groups.

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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.

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The Garden at Celeste. Photo via Facebook

The Garden at Celeste

Moving from the huge and expansive to the tiny and intimate, 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 drinks like the "Midlife Crisis," a combo of Mezcal, coconut, and pineapple.

GreenRiver

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.

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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.

Vertigo Sky Lounge

We prefer our rooftop drinks a bit more calm and a bit less bottle service, but for those into the scene, Vertigo is one of the top places to go. Billing itself as a "party lounge," Vertigo lives up to the sales pitch, with a packed house on weekend evenings filled with revelers cruising for their next makeout session. Kidding aside, though, it's a gorgeous space, and if you can get a seat by a fire pit, hang on to it for dear life.

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The interior of Cindy's. Photo via Facebook.

Cindy's

This rooftop bar atop the Chicago Athletic Association hotel boasts incredible cocktails by mixer Nandini Hhaund, 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. Best of all, they've just launched their new lunch menu, so if you don't want to fight the crowds, stop in for a mid-day indulgence.


Fountainhead

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 (now run by Chef Sean Sanders) and there is literally no other rooftop bar in Chicago with a selection of drinks as good as this one.