The Robey

Milwaukee Avenue runs north-west across Chicago's grid, and where it meets North and Damen it leaves wedges at the corners. In 1929 one of them got the Northwest Tower, 203 feet of Art Deco offices marketed to doctors and lawyers; the Flatiron Arts Building across the junction is the same shape for the same reason. In the tower rooms the sash windows are framed in black, and the bathroom is walled off in dark green panelling and wired glass. A red steel nightstand with marble shelves hangs off a pole by the bed, beside a drawing of a candlestick telephone, the kind the first tenants would have answered. Next door, the Hollander Fireproof Warehouse of 1905 holds 20 of the 89 rooms, the Annex Lofts: plywood bunks on black steel poles against whitewashed brick.

Recommended for couples and friends who would take a neighbourhood over the Loop, and for families of four in a Queen + Bunk Loft. The Loop is fifteen minutes on the Blue Line from Damen, a minute from the door, though there is no hurry: Wicker Park's bars and restaurants are a walk away, and the 606 elevated trail is a mile and a half on a Tokyobike, lent free. The pool on the warehouse roof shuts for winter and reopens in May, with Solana's tacos and frozen cocktails beside it. Rates are room only, which Café Robey softens by doing brunch all day. The Up Room, on the 13th floor, keeps the skyline for over-21s, and Clever Coyote mixes tiki drinks in a nineties spirit, fair enough in a tower once called the Coyote Building.