Heart O' Chicago Motel

Forget all the fuss about modern amenities—it’s the Heart O’ Chicago’s retro vibe that makes it so charming. Built in 1959, this Edgewater motel retains its cusp-of-the-’60s aesthetic, right down to the iconic neon sign (complete with a heart where the O should be). There’s plenty of appeal outside the comfortable rooms, however: Hop on the Clark bus for a quick ride down to Wrigley Field, or take a quick stroll to the bustle of Andersonville’s nightlife scene or the peace of Hollywood Beach. Staying in? No problem. Expect clean rooms, free Wi-Fi, a complimentary continental breakfast and the lure of the White Castle next door.