Here's Our Travel Guide to This Nation of Over 7,000 Islands
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.
1. Roof on the Wit201 N State St, Chicago
2. Vertigo Sky Lounge2 W Erie St, Chicago
3. 52eighty166 E Superior St, Chicago
4. IO Urban Roofscape127 W Huron St, Chicago
5. Drumbar201 E Delaware Pl, Chicago
6. J. Parker1816 N Clark St, Chicago
7. Plymouth Restaurant & Bar327 S Plymouth Ct, Chicago
8. The Signature Room at the 95th875 N Michigan Ave, Chicago
9. Studio Paris59 W Hubbard St, Chicago
10. The Garage Bar & Sandwiches6154 N Milwaukee Ave, Chicago
Do you like models, bottle service, and DJs? If so, theWit's rooftop lounge is for you. More than just a glitzy bar, the 27th-floor hotspot features a retractable roof (it's open year-round, after all), a 3D video-mapping wall, and a sleek bar that turns into a runway. The food and drink menu is equally fit for a glam squad, serving up flatbreads, seafood towers, fancy craft cocktails, and punch bowls.
On the 26th floor of the Dana Hotel, this rooftop lounge is one of the best party spots in the Chicago hotel bar scene. In the winter, Vertigo turns into an indoor/outdoor ice bar where you can do necessary winter drinking activities like take shots on an ice luge. The rest of the year, it returns to its ultra-luxe penthouse vibe with DJs, bottles of Cristal, buckets of beer, and an outdoor fire pit.
52eighty, on the 29th floor of the MileNorth hotel, is a rooftop bar with a sleek indoor lounge and enclosed outdoor patio. This lesser-known spot is open all year-- high glass walls protect you from those Lake Michigan winds. 52eighty 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. Closed for winter season.
This seriously sleek rooftop spot is perfect for our 100 days of Summer. A lounge with swanky drinks and serious eats, this is the place to be when the weather's nice.
Not only is Drumbar one of the sexiest rooftop lounges in Chicago, the 18th-floor bar atop the Raffaello Hotel has a brag-worthy selection of whiskey, scotch, bourbon, and cognac. The sleek spot has a cozy den-meets-gentlemen's club decor with dark leather couches, wood-paneled walls, and a marble bar. During the summer, the seasonal outdoor patio makes it even more of an after-work drinking destination near the Magnificent Mile.
This rooftop bar atop the Hotel Lincoln features an impressive cocktail list, views of the park/lake shore/skyline, and small bites so good you'll hang around for a dangerously long time--no big deal.
Plymouth Restaurant & Bar is a popular after-work spot in South Loop with a rooftop on the third floor. Flanked by John Marshall Law School and the Harold Washington Library, the rooftop goes year-round courtesy of a heated 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.
This fancy schmancy bar and restaurant on the 95th floor of the John Hancock Center boasts panoramic city views through massive floor-to-ceiling windows. The Signature Room is probably Chicago's most jaw-dropping location for drinks, but beware: the prices are steep. It doesn't really matter what you order -- be it a martini and high-end tater tots or champagne and a seafood tower because after all, you're there for the ambience.
French-inspired fare headlines this bistro in Chicago's River North neighborhood. Get Francophilic with a selection of fine French Champagnes, updates on classics like chicken paillard and short rib bourguignon, and tons of shellfish, including Le Grand Plateau with lobster, oysters, snow crab claws, shrimp, and king crab.
The Garage Bar & Sandwiches is a gastropub offering 130 beers, free Wii, shuffleboard, and sandwiches named after Steve Martin. It doesn't stop there-- the industrial venue also includes a roof deck. Yes, there is no heat. And yes, service may be limited. But the patio at this Norwood Park neighborhood gem doesn’t officially close in the winter, which means you can keep going up there for as many winter months as you can handle it.