Romance Nightlife in Chicago

Are you and your special someone looking to get away for some romantic one-on-one time? Chicago will provide you with beautiful hotel suites, elegant food, and a wonderful selection of bars and lounges to enjoy a romantic evening together. Couples looking for a spectacularly romantic evening will love sipping drinks at C-View on the 29th floor of the Affinia Hotel, while overlooking the sparkling lights of the city. Or, go back in time to experience the beauty of French colonial Southeast Asia at Le Colonial in the swanky Gold Coast. Continue to Pops for Champagne to get carried away by live jazz music with a nice glass of bubbly. And, those looking to have a night with style, enjoy a cocktail in Donald Trump's plush cocktail hotel bar, Rebar. For a fancy yet casual feel take your date to Redhead Piano Bar to listen to some old faves, while getting close over a bottle of wine. Couples who want a romantic neighborhood experience should not miss the elusive Violet Hour in Wicker Park, designed to bring you an old-fashioned speak easy with some of the best cocktails in the city! Wine lovers will feel some loving warmth over a fine glass of wine at the cozy wine bar, Webster's Wine Bar. For a more lively evening head to the infamous Green Mill to swing together to the best live tunes in the city. Finally, go the alternative route with a night of saucy dancing at Rumba, or some artistic bonding at the Music Box Theater.

C-View at the Affinia Hotel

166 E. Superior St.

Colonial (Le)

937 North Rush Street

An escapists paradise in the heart of the Gold Coast... read more


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401 N Wabash Ave
at Trump International

Trump's swank hotel bar... read more

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Pops For Champagne

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601 N State St

Upscale River North Champagne Lounge and Jazz Club... read more

Redhead Piano Bar

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16 West Ontario Street

Wine by the piano... read more

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The Violet Hour

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1520 North Damen Avenue
Between Pierce Avenue & Wicker Park Avenue

A Take-Note Bar... read more

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Webster's Wine Bar

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1480 West Webster Street
Between Clybourn Avenue & Dominick Street

Fine wine bar... read more

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Green Mill

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4802 North Broadway Avenue
At Lawrence

Swinging former speakeasy... read more


351 West Hubbard Street

South American Fare... read more

Music Box Theatre

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3733 North Southport Avenue

Historic movie house... read more
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