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Chicago's Best Wine Bars

A wine bar is a great date environment to unwind, relax, and enjoy conversation. Chicago is full of swanky wine bars and lounges, and we've picked the best for your date night.


Webster's is one of Chicago's oldest wine bars. Recently shutting down its Lincoln Park location to open up in Logan Square, it features tastings and events perfect for a date night. Events include 2nd Story, a hybrid storytelling series that incorporates music and true tales from local writers. For an extra fee, purchase a wine flight of four selections meant to complement each story. Time Out Chicago says, "We’ve missed many a movie because we stopped by this funky wine bar across the street from Webster Place theater for a pre-show cocktail. When tasting pours are this affordable (and interesting), we pretend it’s for educational purposes and stay all night, soaking up the dark, Bohemian vibe and munching on tasty cheese plates. We’ll catch the movie on Netflix."
Address: 2601 N Milwaukee Ave, Chicago, IL 60647


The beautiful historic Walnut Room has been a Chicago tradition since 1907. Located on the 7th floor of Macy’s on State Street, the Walnut Room is the first restaurant ever opened in a department store. The wine bar added to the decades-old Walnut Room in 2007 is really just a corner of the dining area, and it’s only open when the restaurant is (read: to align with ladies who lunch, not ladies who Red Bull and vodka). But it’s a nice spot for a midday or after-work drink, full of the restaurant’s characteristic dark wood and formal-yet-friendly service. Nicer still is the wine list, which has a staggering number of bottles under $30 and more than 20 wines by the glass.
Address: 111 North State Street, Chicago, IL 60602

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