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Chicagoan here. Trying to make suggestions outside of the Michelin ones cuz we all know about those. Places are usually in River North, Fulton Market, or Wicker Park.

For a chill yet upscale night out: Signature Room on 95th (view is fantastic), London House, Terrace 16, Three Dots and a Dash.

For a nice brunch: 3 Arts Cafe (fancy option), Wildberries (cozy casual option), Le Colonial for French inspired Vietnamese (in the middle option).

Niche options: Andy's Jazz Club for live jazz performances, Omakase Yume/Sushi San/Nobu/Roka Akor/Momotaro for sushi, Fogo de Chao (Brazilian)/Daebak (Korean)/Gyu Kaku (Japananese) for BBQ, Aba for Mediterranean.

 

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