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Embrace your inner Chicagoan and offer to split what’s been called the city’s sauciest, doughiest, cheesiest deep-dish pizza at Giordano’s.
Or pledge your allegiance to Pizzeria Uno, the inventors of the deep dish. Impress your date by reserving spots at one of Chicago’s two 3-star restaurants, Alinea or L2O.
Webster’s Wine Bar, one of the city’s first wine bars, is a cozy, classic option.
Chicago’s blues, soul and jazz are legendary, but it’s also the birthplace of house music and has a booming indie scene.Become wine snobs together and sign up for a wine tasting (or winemaking) class at City Winery Chicago.If you’re not into wine, Maude’s Liquor Bar serves great cocktails in an intimate setting.The Green Mill Cocktail Lounge is a favorite of trendsetters and old-school jazz aficionados.Swing music fans should stop in on Tuesday or Thursday nights.