The Blackstone

This gorgeous hotel, first opened in 1910, has had an intriguing run so far. Many U.S. Presidents have stayed there (including Teddy Roosevelt), it was a favorite hangout of Al Capone and his cronies, and Maharishi Yogi, the Beatles' personal guru, once owned the building. Now part of Marriott’s Autograph Collection boutique imprint, it's simply one of the most beautiful hotels in the Loop and a favorite for bands playing at the nearby Lollapalooza music festival in August. Don't miss the attached Spanish small-plates restaurant, Mercat a la Planxa.