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The Best Rooftop Bars in Chicago

The Best Rooftop Bars in Chicago

Chicago summers call for expanding your repertoire beyond Jimmy's and the Pub and venturing out to enjoy the weather atop one of the city's countless rooftop bars. Whether you're taking in sweeping views of the Loop and Lake Michigan from a Downtown rooftop, or enjoying a drink on the second story of a Wicker Park or Logan Square joint, keep reading for some of our favorite rooftop bars in the city.

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1. Cindy's Rooftop

Cindy's is a classic and our love for the rooftop restaurant and bar has been extensively documented in the past. Do yourself a favor and swing by in the summer, when sunlight hours stretch longer into the evening and you can still enjoy a glittering view of the Lake as late as 7 or 8pm while sipping on one of their expertly crafted cocktails.

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2. London House

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Lots of nights should end on the 22nd floor of London House, where views of the Lake, the Chicago River and Magnificent Mile can be enjoyed alongside bites off of their new American menu and extensive list of cocktails. Reservations may be required, so check the website in advance before you head out for the night.

3. Raised 

Check out Raised for waterfront views of Downtown and an indoor/outdoor roof terrace. The menu has a fair amount of shareable platters and punch bowls, making it the perfect destination for group outings. They also have a "VIP greenhouse" which sounds pretty cool if you're willing to figure out what it takes to be a VIP. 

 

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4. Fountainhead 

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Fountainhead's rooftop garden boasts a mouthwatering menu of charcuterie boards and cheese platters to accompany their impressive (and extensive) roster of beers and whiskeys.

5. Waydown 

Waydown is the Ace Hotel's rooftop bar and lounge. Featuring live music every week, Waydown is the perfect spot to grab drinks with friends and split a round of Guajillo Short Rib Nachos or Chips and Guac. Better yet, you can grab a burger, cocktail or a beer and shot combo for only $6 on Mondays!

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6. Gene's Sausage and Delicatessen

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Stop by Gene's rooftop beer and wine garden to sip on seasonal beer selections on tap or a glass of red or white while you enjoy a plate of pierogi, schnitzel, bratwurst, goulash or shish kebab–whatever suits your fancy! Better yet? Gene's is located right in the heart of Lincoln Square, so there are plenty of other places worth checking out!

7. Drumbar

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Drumbar has a speakeasy feel and specializes in cocktails. Test out a house speciality like Chamomile Ketel Soda (chamomile infused vodka with Cocchi Americano, blackberry lemon and soda) or their Cucumber Margarita (tequila with japapeño infused St. Germain, Avéze, salted cucumber and lime).

8. The Up Room 

Enjoy cocktails on the 13th floor of Wicker Park's art deco-era Robey Hotel at the elusive The Up Room. Shift between the bar, lounge and terrace for one-of-a-kind views of the city that overlook Downtown. This venue is fairly intimate, so dress up and make a night of it.

 

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9. Streeterville Social 

Swing by this massive outdoor terrace on the third floor of the Loews Hotel Downtown for $5 Rosé by the glass on Wednesdays, boozy popsicles or brunch on the weekends. This is the perfect spot to start or end your night and can accommodate a larger group or party.

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10. Whiskey Business 

Last but certainly not least, Whiskey Business is a Wicker Park nightlife staple. The restaurant, bar and rooftop mixes "80s and 90s nostalgia with over 115 different whiskeys," so prepare your liver and get ready for a night of dancing to some great throwback tracks.

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