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Over a century ago, this Michigan Avenue landmark served as home base of the Chicago Athletic Association. The building had been vacant since 1997, so it was a pretty big deal when design firm Roman and Williams stepped in to re-imagine the massive building as a slick 241-room hotel. Sport is still a prominent theme here, as evidenced by a tricked out game room and walls of museum quality athletic memorabilia. And while the stained glass windows, grand ballroom, and general clubbiness were left intact, the brass lighting fixtures and leather furniture (both in-room and throughout the hotel) are welcome additions. There’s also the sexy rooftop restaurant, Cindy’s, a Shake Shack, and three more places to eat and drink. Incidentally, the cozy library at Cindy’s is an excellent place to host a private event—it doesn’t feel at all like a corporate hotel space, and the views of Lake Michigan are jaw-dropping.

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