Chicago's Vertigo Sky Lounge, dana hotel & spa

Vertigo Sky Lounge atop the dana hotel & spa (Courtesy Vertigo Sky Lounge)

Chicago's Best Rooftop Bars

By Sarah Perkins on 07/13/15, updated 05/23/16
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Chicago's restaurant clout has hit a high, and it's equaled only by the bars and lounges. A hub of secret tippling activity during the Prohibition era, Chicago now has a well-known and well-publicized cocktail culture. From the sports-obsessed Wrigleyville strip to the swanky, see-and-be-seen clubs in River North, there truly is a watering hole for everyone. For the spots that come out on top, just look up. Rooftop bars are taking over, and everyone wants to be above the cut (and the sidewalks). They're the perfect places to take in some sun and fun during the afternoons, or for a nightcap overlooking the sparkling cityscape. We've rounded up some of our favorite Chicago rooftop bars and lounges. Even if you're afraid of heights, the views, inventive menus and cool atmospheres will keep you grounded. 

Vertigo Sky Lounge

(Courtesy Vertigo Sky Lounge)

Nightlife

Vertigo Sky Lounge

Vertigo isn't just a fair weather destination—head over in the winter to experience the city's only outdoor rooftop ice bar. The cocktails and fire pit will keep you plenty warm on the plush lounges at this River North spot. Don't worry if you'd rather stay inside; there are still plenty of views from the floor-to-ceiling windows.

ROOF at theWit

(Courtesy ROOF at theWit)

Nightlife

ROOF

This rooftop is consistently named one of the best in the city, and is quite the chameleon, especially with the four-season retractable roof option. Relax during Movie Mondays in the summer, turn your Sunday into a "Funday" in the afternoons with live DJ sets, or even catch a fashion show here.

Streeterville Social at Loews Chicago

Streeterville Social (Courtesy Loews Chicago Hotel)

Activities, Nightlife

Streeterville Social

While this isn't the city's highest rooftop bar, it is the largest at a whopping 9,000 square feet. The surrounding architecture is all Chicago, but the menu leans tropical, like the custom mai tai and a "Pink Page" fully dedicated to rosés with and without bubbles. Sip and swing on the birdcage chair or play a lawn game on real grass.

Rock Bottom Restaurant & Brewery

(Courtesy Rock Bottom Brewery)

Restaurants

Rock Bottom Restaurant & Brewery

The Chicago location of this all-American chain features a rooftop bar complete with high-top tables and local beers brewed on-site (which you can also take to-go in a growler). Celebrate your love for hops with beer events throughout the year, including specials and behind-the-scenes looks at the brewing process.

Celeste

(Courtesy of Celeste)

Restaurants

Celeste

Step back in time on top of Celeste's multi-level, turn-of-the-century lounge. The Garden is the venue's ode to Victorian England, complete with ivy-covered walls and antique decor. The rooftop is the only floor to not only have house cocktails, but also special frozen cocktails like the Electric Piña Colada and Nuclear Caipirinha.

Drumbar

(©Anthony Tahlier)

Nightlife

Drumbar

Travel in a specially designated elevator to the top of the Rafaello Hotel for craft cocktails in a sophisticated atmosphere. The inside emulates a cozy study, the outside a green-and-white breezy patio. The cocktail menu ranges from savory and smoky to fresh and tropical, with witty names like All About that Trace and Tropical Camping.

Terrace at Trump

(©Neil Burger)

Nightlife

Terrace at Trump

If you're looking for lake and river views, this is your spot. You'll also come face to face with the Wrigley and Tribune buildings. The upscale space adds special touches to its craft cocktails, such as blue pea flower ice cubes, well worth the price tag. Classic liquors include 25-year-old scotch and an extensive wine list.

Virgin Hotels Chicago

(Courtesy Virgin Hotels Chicago)

Hotels

Virgin Hotels Chicago

The Virgin Hotels Chicago's Cerise moniker is French (for red), the menu is Japanese izakaya-inspired, the whimsical decor is all Sir Richard Branson. The rooftop overlooks the surrounding Loop's incredible architecture. Want to escape the scene? Head downstairs and look turn left—there's a quiet patio with another bar.

Zed451

The dining room fireplace (Courtesy Zed451)

Restaurants

Zed451

When you're not indulging in the extensive Brazilian steakhouse menu, check out Zed45's pagoda-covered rooftop. The cocktail menu favors Latin flavors with sangria, caipirinhas and margaritas. Multiple bars keep the drinks flowing. Wood touches and real grass add a rustic, natural feel.

Raised Bar Chicago

Raised looks out onto the Chicago River (©Isaac Maiselman with The Photographers Gallery)

Nightlife

Raised

Try this hotel terrace for brunch when the views down the river include sightseeing boats and yachts. Try bagel chips and lox, vegetable hash, and an assorted muffin basket served with jams and local honey. Don't worry, there's also a Bloody Mary or Mimosa "toolbox," with fixings enough for four people.

Map of Chicago's Best Rooftop Bars