The West Loop can be overwhelming, with lots of crowded places full of people who seem like their entire lives are hinging on the amount of fun they’re having tonight. This is not the case at Eleven Eleven, an upscale spot that’s relatively relaxed. They have a long wine list, and (if you want) the bartenders will talk to you extensively about the the selection. But there’s also a very good food menu, with options like lamb sausage stuffed peppers, cheese and charcuterie, and a collard green grilled cheese that tastes like something your stoner roommate who’s also a very good chef would make after a night out.
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Gibsons Italia, in River West, is the trendy Italian sister spot to Gibsons Bar & Steakhouse.
Saint Lou’s Assembly
Saint Lou’s Assembly is a throwback restaurant reminiscent of a 1950′s cafeteria-style meat and three. It also has an excellent outdoor patio.
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Ella Elli is a small plates restaurant and wine bar in Lakeview that is great for date night.
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