Wicker Park's sole hotel is set in a 1929 art deco former office building. The 69 tower rooms run small but have comfy beds, lots of sunlight and great city views; the 20 annex loft rooms have a barebones-industrial vibe, with polished concrete floors and furniture made from pressed wood and metal pipes. Staff are friendly and there's free wi-fi.
There's a summer-only rooftop swimming pool and lounge, a top-floor cocktail bar and a full restaurant on the ground floor; guests can work out at the Bucktown Athletic Club next door. It's pricey for the area but the location can't be beat – the bars and restaurants of Wicker Park are at your feet and the L train is around the corner (which means light sleepers might want to look elsewhere).