Ummo is a fun Italian spot in River North that's a respite from all the neighborhood clubstaurants. The open dining room is consistently packed—from couples twirling forkfuls of cacio e pepe to larger groups tackling a 34 oz. dry-aged steak. But while the standards are tasty, the more creative dishes are the main draw. Lobster ravioli floats in a creamy butter sauce with bottarga, and the playful, tomato-shaped pomodoro e basilico dessert is a must-order optical illusion. And if you're looking for post-dinner plans, just head upstairs—the second-floor lounge has a DJ, pool table, and lots of couches.

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