W Chicago City Center

This stunning Beaux Arts building, which started out as a private men’s club in 1929, has been transformed into one of Starwood’s sleek W Hotels. The 369 rooms come with pillow-top mattresses and the option of an in-room shiatsu massage. You can request just about anything (legal) you desire from W’s signature Whatever/Whenever service, which once reportedly hired a helicopter to fetch a guest’s wedding cake. High-speed internet (free wireless in lobby; $14.95 via cable in rooms).