Staypineapple Chicago

Historic hotel in The Loop

Housed in the landmark 1890s Reliance Building (prototype for the modern skyscraper), this hotel's slick, historic design woos architecture buffs. Deco-style lights, iron-filigree stair railings and mosaic-tile floors prevail in the public areas. In the smallish rooms, big windows and pops of whimsical, bright-hued art liven up the warm wood decor. Free bicycles for zipping around town are handy.

A daily amenities fee ($15) offers guests wi-fi, coffee and cupcakes. History factoid: Al Capone’s dentist (and partner in crime) used to drill teeth in Room 809.