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Best Chicago Rooftop Lounges

By Greg Wahl

May in Chicago typically offers an early taste of what is sure to be yet another awesome summer in the ultimate Midwestern city. For one thing, the increasingly warmer weather signals the re-emergence of the city's many rooftop lounges, as nightlife options sprout from hibernation like weeds from a sidewalk. The city's rooftops are inherently romantic at this time of year, with abundant glimmering views of the skyline, stars and swell-looking people. Yes, the roofs often have restrictive reservation policies, get easily overcrowded, and charge a premium for the minimum, but the vibes and the breezes and the boozes often go a great distance toward making up for the fusses. Here's a selection of the city's finest upper-floor hangouts to sip, be seen, and gaze upon the wondrous urban canopy beyond.

iii forks

III Forks Prime Steakhouse

333 E. Benton Pl.
Chicago, IL

The recently-opened local outpost of the small III Forks chain has an expansive (and, yeah, a little expensive) rooftop overlooking the rather weird and pedestrian-unfriendly condo canyon known as Lakeshore East. Night is the best time to lounge here, as the city lights envelop the panorama beyond the long bar and patio cabanas. While dinner at the restaurant below can be a savory wonder, this spot stands out locally, as there is very little to compete (aside from, perhaps, Millennium Park) with the pure lounge-ness of the swanky scene upstairs.

DrumBAR Chicago

201 E. Delaware Pl.
Chicago, IL

Ok, this place isn't open yet, but the location and boutique character of the Hotel Raffaello alone is enough to earn a recommendation. Based on the proposed concept (the bar is set to open next month), a visit to DrumBAR should be a memorable one. Especially more so than the raging Rush Street scene a few blocks west. Anyway, while most outdoor venues tend to lean toward summery drinks to complement the breezy vibes, DrumBAR's drink selection focuses on the toasty amber liquids more closely associated with chillier climates. This is in part due to the "speakeasy" theme going on here, but, with the Pelago-sourced small plates, boutique vibe, and choice location, this is going to be the under-the-radar hotspot of the Gold Coast summer.

Epic Sky

Epic Sky

112 W. Hubbard St.
Chicago, IL

If a downtown Miami-esque Chicago experience is your objective, the upstairs at Epic on Hubbard Street will likely fulfill those expectations. Rest assured, there's some comfortable space, some plants, and a fair amount of sociable sorts awaiting your arrival. Cabana space is available on first-come, first-served basis, so its best to show up early. Despite its River North location and clubby vibe, no bottle service is required, so you can chill without having to drop those extra Benjamins.


Rock Bottom Restaurant & Brewery

1 W. Grand Ave.
Chicago, IL

While it's probably the least fancy rooftop on the list, it does have the advantage of a great location and a good selection of beers. It certainly does provide a proletariat alternative to the chi-chi joints that comprise most other rooftop options. In any case, its a solid option among the River North riff-raff, and a solid bet for an affordable spring/summer evening happy hour.

ROOF thewit


theWit Hotel
201 N. State St.
Chicago, IL

ROOF at theWit made a big splash on the downtown scene a couple years ago, and was instantly almost too popular for its own good. The main complaint here was the line, which may not be quite so bad this year, as competition has sprouted on a few other rooftops nearby. If you've walked down Lake Street past State at around 5:00 on a Friday in nice weather, you'll know what I mean. And the line comes complete with clipboard/headset doorman dude standing sentry-style before the first-floor entrance. But, for the rooftop-determined, in this case, the ends justify the meanies. ROOF is splendid and chic and will erase all memory of the half hour spent on gritty Lake Street so far below.


Terrace at Trump

401 N. Wabash Ave., 16th Floor
Chicago, IL

If you've got a fully-loaded money gun, and are prepared to fire away at a special occasion, the Terrace on the 16th floor if the Trump International Hotel Chicago is the place to do it. Strategically designed (I'm guessing) to provide parallel views of the architecturally excellent Wrigley Building next door, as well as the distant lake, winding Chicago river and Loop skyline, the Terrace makes the most of its prime real estate. Reservations might come with a steep food & beverage minimum, but stopping by for a couple drinks on a particularly fine evening is a huge value proposition, as the Donald might say.


Vertigo Sky Lounge

2 W. Erie St.
Chicago, IL

Of course, there is a strong contingent of River North rooftops on the list, but its hard to deny the appeal of the positive comfort and viewables that await the Vertigo visitor. The sleek (yet affordable) dana hotel & spa has multiple positive attributes, and not the least of which is its 26th floor semi-outdoors bar/lounge. While it has a reputation for Jersey-Shore-style dubiousness, the location, staff, and relaxing views & amenities more than make up for it.



739 N. Clark St.
Chicago, IL

The ZED experience is a unique one, including from their contemporary take on the Brazilian steakhouse motif. Cocktails and vibe are a strong element up on the roof, with lots of woods and greenery to offset the urban angles that surround this funky, fun scene. The best bet is dinner inside first, and drinks outside after. Not wildly expensive, and a scene that pretty much anyone could appreciate. They also have shuttle buses if you're thinking ahead on the smart transportation tip.

Greg Wahl is a Chicagoan and urbanophile, and he's usually the guy on the rooftop pointing out constellations.

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