On-trend boutique property with historic bones.

Home to the Pump Room, alas. The fabled restaurant still exists, but it’s now called Booth One.

Opened in 1926 as the Ambassador East, and known until recently as the Ian Schrager–run Public, this Gold Coast classic was recently rebranded as The Ambassador. Where once you might spy Frank Sinatra holding court in his booth at the Pump Room, or Marilyn Monroe clicking across the lobby’s marble floor, now you’re more likely to find media types pecking their iPhones under the dripping chandeliers and dentil moldings of the white-on-white lobby. The 285 rooms forgo historicity in favor of low platform beds, midcentury furniture, and a low-wattage palette enlivened by artworks on paper and poofy pillows. The Pump Room itself has been redubbed Booth One (a nod to Old Blue Eyes’s favorite table) and is managed by Lettuce Entertain You, the Chicago catering conglomerate.

You want a reasonably priced, well located hotel that pairs smart style with Midwestern unpretentiousness.

Borrowing one of the hotel's gratis bikes, you pedal over to Lakeshore Drive and point your front wheel toward the Art Institute. American Gothic, here we come!

Booth One - Modern American cuisine in a nostalgia-tinged setting

Library Coffee Bar - Baked goods and exotic coffees