We loved this property’s 19th-century, retro-vintage vibe, with the scent of leather and tobacco in the air, dark wood and gentlemen’s racquets club feel. No accident of course, because this Venetian Gothic building was indeed once a prestigious club. Rooms are bijou, but we figured that since we’re in a fun-filled city, we wouldn’t be spending much time in them anyway.

12 S Michigan Ave, Chicago