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The 10 Best Rooftop Bars In Chicago, 2014 Edition

By Staff in Food on Apr 16, 2014 7:50PM

Last year's list of the best rooftop bard in Chicago mixed popular downtown spots with unique locations in the neighborhoods and we're hoping this year's list matches the quality of 2013. We've updated a few favorites from the past but also included some fresh faces as well this year.

Without further ado we present this year's list. As always, debate, discuss and dissect and leave your recs in the comments.

The rooftop at Little Goat Diner. (Photo via Little Goat Diner's Facebook page.)

Little Goat Diner
Comfort reigns at Stephanie Izard’s Randolph Street diner and when the weather is pleasant the rooftop’s tables and seating is even more in demand than the restaurant’s booths. Enjoy the full a limited food menu from Little Goat on the rooftop separate from the regular menu while gazing at views of the downtown skyline and with the bustle of Randolph Street’s dining district a fading memory. — Chuck Sudo

Little Goat Diner is located at 820 W. Randolph St.

Nestled next to the bustling intersection of Montrose and Damen, Fountainhead is a perfectly fine place to grab a meal and drink during any season. But head up during the summer months in Chicago and you find one of the best neighborhood rooftops around. Although it can get crowded, rooftop seating never feels cramped, the layout allowing a nice flow rather than cramming in as many tables as possible. And while you get a lot of natural sunlight, there is still a good amount of shade so you aren’t broiling in the summer heat. Fountainhead has a stellar craft beer and whiskey selection, perfect for sipping the afternoon away. The menu changes seasonally and Chef Cleetus Friedman is dedicated to offering up a lot of local flavors and purveyors to spotlight. A relaxing neighborhood spot that supports lots of local folks in the food and beverage community makes Fountainhead a quintessential Chicago spot. — Lisa White

Fountainhead is located at 1970 W. Montrose Ave.

Homestead On The Roof
They grow some of the ingredients for their excellent menu here up on this beautifully landscaped garden roof in West Town. A perfect place to savor treats like crispy chicken skins and creamy egg duck carbonara on a nice summer evening. — Melissa McEwen

Homestead On The Roof is located above Roots at 1924 W. Chicago Ave.

the view from Terzo Piano's rooftop. (Photo credit: chicagogeek)

Terzo Piano
Even if you don’t like art you should pencil in a trip to the Art Institute’s Modern Wing during the warm weather months and enjoy one of the best views of the Chicago skyline around. While you’re there savor some food and cocktails from Tony Mantuano’s team—another manner of enjoying Chicago’s world class culture. —Chuck Sudo

Terzo Piano is located at 159 E. Monroe St.

Oh, if the walls could talk at drumBAR (located on the 18th floor of the Rafaello Hotel in the Gold Coast). The building first opened in 1926 as an apartment building called the Hampshire House. It was used as a nursing students residence during World War II and remained that until the early 1970s. After converting the apartments into a hotel, they promoted the top floor (where drumBAR sits now) as the ultimate penthouse “with 24 foot ceilings, two bedrooms, formal dining rooms, a paneled office with a bar hidden by moveable bookcase and of course, the outdoor terrace with views of Lake Michigan.” Imagine all the real-life Don Drapers that did Don Draper adult activities in that penthouse during those crazy 1970s. While you can still get a sense of that history in the inside of drumBAR, the terrace successfully helps keep one foot in the past and one in the present with a comfortable, relaxing spot to enjoy a drink. You can certainly do your own time travel by ordering classic cocktails from the outstanding bar (not hidden behind a bookcase) that’s headed by Alex Renshaw. As we mentioned last year, you can beat the crowds by visiting earlier in the week. — Paul Leddy

drumBar is located at 201 E Delaware Place

Shanghai Terrace
The Peninsula’s Shanghai Terrace rates as my favorite rooftop bar because it’s not just a rooftop bar. It’s that rare commodity even rarer perched atop a swank downtown hotel: an actual escape. The dim sum is the best outside Chinatown, followed by traditional Cantonese desserts like sweet almond broth and bird’s nest soup perfect for pairing with cocktails almost—but only almost—too pretty to drink. The times I’ve visited, the space has retained its hushed lantern-lit intimacy, meaning this is one rooftop watering hole remaining relatively fancy-free of the ick factor than tends to metastasize so many stories up on Chicago’s most resplendent nights. Extra bonus: The staff shower you with your choice of pashminas if the evening does become a chilly one, allowing you to lounge in peace that much longer. —Melissa Wiley

Shanghai Terrace is located at 108 E. Superior St.

ROOF on the Wit. (Photo credit: Karl Klockars/Chicagoist)

ROOF On the Wit
Since opening in 2009 this rooftop bar has impressed tourists and locals alike with its two outdoor patios, an indoor lounge with full bars, fireplaces, a small plates menu featuring fire-baked pizzas and a 27th-story bird's eye view of State Street. And really, isn’t that all you need? —Chuck Sudo

ROOF on the Wit is located at the Wit Hotel, 201 N. State St., 27th Floor.

IO Urban Roofscape
Stepping off the elevator leading into the IO Urban Roofscape bar (located on the 4th floor of the new Godfrey Hotel), it can feel like you are stepping into the spit personality of nightlife in Chicago. On one side of the bar, is the indoor, lounge scene. The vibe here is mellow and comfortable. On the other side of the bar is the outside deck with a great view of the city. The space even has a retractable roof for those tricky Chicago weather days (which, as we all know, is all the time). What is most interesting to me, however, are the cocktails. Chef Riley Huddleston - who has logged some time at The Aviary among other Chicago properties - oversees the food and beverage program. At IO Urban Roofscape, he has compiled a unique and very ambitious cocktail menu that most guests will have no idea the work that goes into each drink that is prepared in the kitchen. Take the bar’s margarita. Though the menu lists 4 ingredients, there are actually 22 that make up the drink. Multiple citrus elements, shrubs, even a habanero salt foam are used to build layers of flavor and keep the drinks very consistent. In fact, so much thought and work has gone into the development of the cocktails that the $10-12 price tag seems like a steal. Whatever side of the split personality you choose to enjoy, you can spend it knowing that the cocktail in your hand is a lot more complex than it appears. — Paul Leddy

IO Urban Roofscape is located at 127 W Huron St.

Vertigo Sky Lounge
This River North hotspot (the second highest in the city) combines comfort, elegance and stellar sights above the street views for a thrilling experience. Enjoy amenities such as fire pits, an ice bar during winter, classic cocktails and a laid-back vibe far removed from the downtown bustle. —Chuck Sudo

Vertigo Sky Lounge is located at the Dana Hotel, 660 N. State St.

Gene’s Rooftop
Besides being an awesome delicatessen and a great place to get German culinary delights, Gene's has one of the sunniest most enjoyable rooftops around during the warmer months in Chicago. The design is very quaint German beer garden, where you can relax and soak up some sun while enjoying a a few sausages and pints. The view overlooks Lincoln Square and an adorable block of shops so it is prime location for people watching as well. Gene's recently posted that their rooftop beer garden will officially open Memorial Day weekend (May 22) so get ready to line up now because the local favorite does get packed. It's still well worth it. Make sure to stop downstairs after you've enjoyed the rooftop and pick up some meats, fresh pretzel rolls and homemade salads from the deli. — Lisa White

Gene's Sausage Shop & Delicatessen is located at 4750 N. Lincoln Ave.