Chicago Athletic Association Hotel

Hyatt heir John Pritzker spared no expense repurposing the 1893 home of the Chicago Athletic Association into one of the city’s most original, not to mention best located, boutique hotels. Local architects Hartshorne Plunkard retained the Venetian Gothic exterior, ornate millwork, stained glass, tiles, and cast-iron reliefs and added Cindy’s, a vaulted rooftop atrium restaurant space styled after a modern Lake Michigan beach house offering stupendous views of both the lake and Millennium Park from its alfresco terrace. Cooper Hewitt award–winning design team Roman and Williams preserved the massive 19th-century working fireplaces and elaborate sports-themed woodwork in the original members’ Drawing Room, filled with vintage chairs, modern sculptures made out of antique sporting trophies, and various books about Chicago sports heroes, politicians, and mobsters. Guest rooms feature stylish riffs on athletic-club culture including leather settees that resemble pommel horses; leather club chairs and sofas, updated versions of brass beds, and national park blankets add to the retro vibe. The famous pool where Johnny Weissmuller swam laps with club members did not survive the transformation (it’s now an event space), but kids of all ages love the huge, dark-wood retro Game Room with bocce balls, billiard tables, and chess.