26th floor at the Dana Hotel, Near North Side
Perhaps Chicago's best-known rooftop party scene, this place offers an exclusive penthouse environment along with the city’s only ROOFTOP ICE BAR (?!?) in the winter. Yup. Add nightly DJs, fire pits, and $25 buckets of beer and you’ve got a serious party on your hands.
27th floor at theWit Hotel, Loop
Named one of the top three rooftop lounges in the world by Travel + Leisure, ROOF has it all: scantily clad runway models (yes, the bar is converted into a runway during fashion shows), a video projection screen, and massive views of The Bean and Chicago River. They’ve even got a telescope, in case you want to see those models a little closer up.
29th floor at MileNorth, Streeterville
With a sleek indoor lounge and enclosed outdoor patio, this lesser-known, year-round rooftop provides a more chill environment when it comes to Downtown options, plus lobster rolls, Wagyu sliders, and tequila-based Arrogant Hot Shot cocktails. Because, duh.
4th floor at the Godfrey Hotel, River North
A relative newcomer to the swanky rooftop scene, this 15,000sqft indoor/outdoor playground features a retractable roof that they close when the weather gets nasty, leaving you with unobstructed city views as you dine on lamb lollichops and truffle mac & cheese. Bonus: $2,400 bottles of Dom Perignon '04 and Adult Candy cocktails with Patron and RTC tea poured over cotton candy. Because, DUHHHHHH.
18th floor at the Raffaello Hotel, Streeterville
This cool, speakeasy-style space mixes black leather sofas and killer views of Lake Michigan/the Hancock with stiff drinks like the whiskey-based Local Option or the tequila-packed Naked Street. And did we mention the shot menu? Because we should.
13th floor at the Hotel Lincoln, Lincoln Park
One of the best spots in the summer moves it indoors (slightly) in the cooler months, which means posting up in the cozy indoor bar for small plates from Paul Virant paired with cocktails like the Retox (bourbon, lemon, cayenne) and Seeing Ghosts (gin, port, lemon, tonic). It's got nice lake views, and the eye candy is nothing to sneeze at either.
Flanked by John Marshall Law School and the Harold Washington Library, this third floor rooftop goes year round courtesy of a heated and enclosed patio that's more working man and less typical Downtown swank. It’s the kind of place where you can get breakfast all day and feta with your fries, if that’s your thing.
95th floor at the John Hancock Center, Streeterville
Massive floor-to-ceiling windows and 360-degree views of the city provide a view that can’t be beat. And with $16 tater tots and $150 pours of Remy Martin Louis XIII, you’re gonna pay for it. Pro tip: hang in The Signature Lounge rather than the white-tablecloth dining room, where prices are a bit less steep. But not by much.
While the retractable roof at this second-floor club (above Paris Club) hasn’t been opened for two years, it still maintains that rooftop feel as you rage to top-tier DJs like Calvin Harris and Martin Garrix 'til the wee hours. By the time you get here for the 9pm opening it will be too dark to see outside, but there’s plenty to see inside.
Yes, they have no heat. And yes, service may be limited. But this Norwood Park neighborhood gem doesn’t officially close in the winter, which means you can still go up there as long as it’s safe to do so. But with an indoor space offering 130 beers, free Wii and shuffleboard, and sandwiches named after Steve Martin, why would you?
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Jay Gentile is the publisher of Chicago INNERVIEW Magazine and a Thrillist contributor whose idea of extreme sports is drinking at 1,000ft. Follow him on Twitter.