Terrace at the Trump

Alfresco dining (and drinking) is as time honored a
Chicago tradition as the Wrigley Field bleachers. This city has an affinity for
sidewalk cafes, rooftop bars and outdoor dining rooms. For those of you who
like to pair sunshine and sustenance or booze with a breeze, we present our
favorite al fresco dining options.

(1072 N. Milwaukee Ave., Noble Square)


Frontier’s 2,500 square-foot outdoor beer garden is a lot
like the restaurant’s exalted big game dishes, stunningly rustic. From gator
ribs to antelope meatballs, this Noble Square paragon is a meat lover’s
paradise. Add an extensive variety of beer, cocktails and an open-air rooftop
to the mix, and you have all the ingredients for a perfect Chicago cookout. Oh,
and executive chef Brian Jupiter is a lot more trustworthy behind the grill
than you’re Corona buzzed neighbor wearing a “Born to BBQ” apron.

Star (1531 N. Damen Ave., Wicker Park)

There should be a Big Star in every American city. The
food is phenomenal. It offers $3 whiskey shots every night of the week. And the
patio seating faces Wicker Park’s Milwaukee, North and Damen Avenue
intersection, which is like a street style Tumblr personified. YOU get to feast
on pork belly tacos while YOUR EYES feast on people dressed like Lenny
Kravitz’s kids. If you don’t think that’s a winning combination, then you’re

Purple Pig (500 N. Michigan Ave., Near North Side)

Purple Pig

Nominated for the James Beard Foundation’s “Rising Star
Chef Award,” Jimmy Bannos Jr. is young, but already a prevailing name in
Chicago dining. The Purple Pig serves meat in its most rustic form and their
wine selection is incredibly expansive. If you actually shop until you drop on Michigan Avenue, the enjoyably
intoxicating aroma of The Purple Pig’s roasted bone marrow is enough to restore

Garden (800 N. Michigan Ave., Near North Side)

If you’ve been leaning a bit too hard on the frozen pizza
and TiVo-d American Idol “date
night,” then rally your better half to NoMI Garden and thank us later. Located
on the Park Hyatt hotel’s seventh floor, this open air balcony will spark your
romantic fire into a blaze the area hasn’t seen since 1871. With a menu that
feature foie fras small plates and mint muddled cocktails, a meal here is like
playing with passion fireworks at the love gas station. You’re welcome.

Ada Street (1664 N. Ada St., Noble Square)

Ada Street

Ada Street renovated its patio last summer, adding another unique element to Chef Zoe Shor’s already ridiculously stylish restaurant. With its picnic motif and artificial grass, the outdoor dining room in this Noble Square charm looks and feels like a backyard barbeque. If you’ve ever been to a summer cookout in Chicago, you know that’s a good thing.

(739 N. Clark St., Near North Side)

It would be difficult to find a more stylish restaurant
than Zed451. Everything on the harvest table is worth your time and servers
will pile on as much braised meat as you can eat. The design flow is uncanny, the
cocktails are especially sophisticated and its buzzing location lends itself to
some of the finest ground level views in downtown Chicago.

RM Champagne Salon (116 N. Green St., West Loop)

RM Champagne Salon

You’ll find RM Champagne Salon’s secret entrance by way of a cobblestone alleyway just off of Randolph Street. If you’re lost, look for a pack of immaculately dressed, recently-engaged types who appear to know when there’s a sale at Barney’s. It’s hard to stay void of pretentions when your champagne menu includes a $1,500 magnum of ’99 Jacques Selosse Milesme Brut, but RM is authentic to the champagne culture and not totally unapproachable for aspiring adults. RM’s outdoor patio, with its gritty Industrial Age feel, complements the restaurant’s Grace Kelly-inspired interior like a glass of 1995 Blanc des Millénaires and hearty Gruyere cheese.

House Tavern (321 N. Clark St., Near North Side)

The “location, location, location” rule of real estate is
just as appropriate for outdoor dining as it is for a two bedroom condominium,
and Bridge House Tavern is a luxury penthouse in London. This alfresco space is
as close to the Chicago River as you can get with actually making contact with
a passing bluegill. Go for the view, stay for the oysters, just don’t go for a

Terrace at The Trump (401 N. Wabash Ave., Near North Side)

Trump International Hotel Tower

Not every amazing view is from the top. Located on the 16th floor of the Trump International Hotel and Tower, The Terrace at Trump is affixed with arguably Chicago’s most spectacular outlook. Diners are situated above the river, parallel with the Wrigley Building Clock Tower, and are given a panoramic sightline of downtown Chicago that extends from the Willis Tower to the Hancock. If you’re looking to sip craft cocktails and, simultaneously, upload a gallery’s worth of Instagram bangers, the Terrace calls your name.

(112 W. Hubbard St., River North)

Do we ask too much of our night clubs? We must, because
EPIC has a seafood menu that’s wayyy too good for a place that thumps Afrojack until
3AM. Besides its delicious eats and bumping beats, EPIC’s third story rooftop
is a good place to cool down after an especially spirited session on the dance

J. Parker (1816 N. Clark St., Lincoln Park)

J. Parker

Appropriately, the view of Lincoln Park is incredible from atop the 12-story Hotel Lincoln. To the east, guests look straight down at the South Pond, Lincoln Park Zoo, and over North Avenue Beach to the Lake Michigan horizon. Looking south, an only slightly disrupted view of downtown Chicago. If the Hotel Lincoln is anchored in timeless nostalgia, then The J. Parker is its dramatic ballast. Tables are cool when they have fireplaces in them. They’re even cooler when surrounded by cabana-style seating. And they’re the coolest when they have glasses of Pimm’s Cointreau mixed sangria sweating on their tops. All you really need to know about The J. Parker is that they have, like, really cool tables.

Aces (1321 W. Taylor St., University Village)

Three Aces 140-person outdoor dining room is an absolute
game changer on Taylor Street. The space is buzzing every night of the week,
but gets especially turned up on theme nights like Hillbilly Bingo and movie

American Junkie (15 W. Illinois St., Near North Side)

American Junkie

There are plenty of options on this list for people who want a quiet dinner under the stars, but this ain’t one of them. American Junkie opened this spring and fast became a downtown go-to for bottle poppin’ – not an easy task in River North, where bottle service receipts blanket the ground like new-fallen snow. The night club’s most distinctive quality is its retractable ceiling. Most clubs’ talk about “blowing the roof of the joint,” this place means it.

Maria’s Packaged Goods Community Bar 960 W. 31ST St., Bridgeport)

With an enormous beer selection and an incredible bar soundtrack, Maria’s is always a party. Oh, and Pleasant House Bakery is right next door, so its Bridgeport location makes for some of the city’s best carb loading. While Chicago’s cocktail culture hovers over Wicker Park and Logan Square like a gin soaked rain cloud, this South Side mainstay is worth the sip trip.

Ultra Bar (1177 N. Elston, River West)

Photo courtesy of Estate Ultra Bar

If you like your outdoor party with elbow room, visit
Estate Ultra Bar and its 4,000 square-foot open air rooftop. Billed as a place
for “social dining and drinking,” this place has all the bells and whistles of
a stylish lounge without the pretentions that go with denying guys like me

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