Upscale Nightlife in Chicago

expert pick

Cafe Spiaggia

980 North Michigan Avenue
Level 2

Cafe elegance on the Mag Mile... read more

Davenport's Piano Bar & Cabaret

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1383 N. Milwaukee Ave
Just south of North Ave

Critically acclaimed piano bar and cabaret...
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1444 West Chicago Avenue
Two blocks east of Milwaukee Ave

Shake your booty... read more

Bar @ The Peninsula Chicago (The)

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108 East Superior Street
(at North Michigan Avenue)

Posh comforts... read more


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1530 N Milwaukee Ave


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401 N Wabash Ave
at Trump International

Trump's swank hotel bar... read more

Green Dolphin Street

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2200 North Ashland Avenue

Swing and groove in this elegant club... read more

The Tasting Room

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1415 West Randolph Street at Loomis Street
Randolph Wine Cellars

100 Bottles of Wine on the Wall... read more

J Bar

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610 North Rush Street
(inside the James Hotel)

Cocktail minimalism... read more

Logan Bar and Grill

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2230 N California Ave
between Milwaukee and Lyndale

Swanky neighborhood bar... read more

Leg Room

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7 West Division Street

Casual dining and martinis on the Gold Coast...
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Junior's Sports Lounge

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726 West Maxwell Street
Between Maxwell & Halstad

Not for the kids... read more


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2210 West Chicago Avenue

Lots of Eye Candy... read more

Kitty O'Shea's

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720 S Michigan Ave
Hilton Chicago

Neat Irish pub doubles as hotel bar... read more

Dave & Buster's

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1030 North Clark Street

Enjoy Playing While Dining... read more

Lucky Strike Lanes

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322 East Illinois Street

Bowling Fun!... read more


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3243 N. Western Ave.
(At W. Melrose)

Quiet enough for conversation... read more

The Leg Room

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7 West Division Street

Martinis On The Gold Coast... read more

Club Republic

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1520 North Fremont

Dance All Night... read more

Climax Lounge

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324 West Chicago Avenue

See & Be Seen... read more
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