1. Stay and Play: Chicago Athletic Association
This restored athletic club touts an interior that packs a punch. Every room oozes art deco old world elegance. Snag a leather-clad spot by the fireplace or admire the ornate marble staircase in the lobby before heading to the rooftop restaurant, Cindy’s, for an unbeatable view. And don’t forget to check out the Game Room on the second floor. Come for the bocce and billiards, stay for the seriously addictive crab hush puppies.