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Congratulations! You made it to summer. First order of business: spend as much time outside as possible--preferably while sipping an icy cocktail and taking in a killer skyline view. (There’s no one more deserving.) Here are ten perfect Chicago rooftops for doing just that.

The Terrace Rooftop at The Conrad

The secluded rooftop at this Mag Mile hotel is a bit of a secret--and a laid-back alternative, where you usually won?t fight for a table or wait for a drink. There?s live jazz, too.

521 N. Rush St.; 312-645-1500 or

Rooftops Trump1

The Terrace at Trump

The Donald’s soaring skyscraper has, hands down, the most dramatic view of any rooftop in town. The selfie you’ll take with the Wrigley Building will almost justify the $20 you’ll pay for one mojito.

401 N. Wabash Ave.; 312-588-8000 or 

Chop Shop

Rooftop scenes are generally dressy affairs, but at this tucked-away roof deck in Wicker Park, you can get away with wearing jeans and gorging on a charcuterie platter or $1 oysters on Wednesdays (5 to 7 p.m.).

2033 W. North Ave.; 773-537-4440 or


The Victorian-inspired spot is open until 5 a.m. on Saturdays. Dress to be seen--especially by the picky bouncers at the door--and share a punch bowl with your girlfriends.

111 W. Hubbard St.; 312-828-9000 or

Cindy’s at the Chicago Athletic Association Hotel

Picnic tables, craft cocktails and Lake Michigan/Millennium Park views make the brand-new restaurant this summer’s must-try.

12 S. Michigan Ave.; 844-312-2221 or

J. Parker at Hotel Lincoln

Rain or shine, a new retractable roof keeps this spot going strong. Head up and you’ll see the zoo, the park, the lake, the city and everything in between. (If you ask us, it’s a tie between this and Trump for number one rooftop view in Chicago.)

1816 N. Clark St.; 312-254-4747 or

Cerise at the Virgin Hotel

The vibe at this new Loop bar is 100 percent sultry, and yes, there is a dress code. If you’re single and ready to mingle, go and nurse a fruity, rum-based Tradewinds Punch cocktail.

203 N. Wabash Ave.; 312-940-4774 or

Drumbar at Rafaello Hotel

Cool down with liquor-infused freeze pops and slushies at this chic, clubby penthouse bar. Two fire pits and views of the Hancock building make it a solid place to take your out-of-town visitors.

201 E. Delaware Pl.; 312-933-4805 or 

Gene’s Sausage Shop

When it’s not quite cocktail hour yet, head to this cheerful neighborhood hangout for daytime beers and brats. It’s a hidden gem atop Lincoln Square’s cutest European market.

4750 N. Lincoln Ave.; 773-728-7243 or


Take your craft beer-fanatic friends to this Ravenswood hangout for an exhaustive list of bottles and drafts. For a high-low approach, pair a refreshing bottle of sparkling rosé with sloppy joes for lunch. 

1970 W. Montrose Ave.; 773-697-8204 or 

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