Go industrial at The Iron Horse (from $149), where spacious rooms feature masculine details like leather headboards and iron hooks, and you can fall asleep to the gentle chug of the railroad that runs next to the building (for a quieter night, book a southeast corner suite facing the warehouse district). Stay up late at the buzzing lobby bar playing a game of billiards on the vintage 1912 table while sipping Manhattans ($10) made with the hotel’s own rye whiskey recipe, Barrel 1907, distilled and barreled in collaboration with neighboring Great Lakes Distillery.
Stay around the corner from Milwaukee Street’s stylish restaurants at the green-certified Hotel Metro (from $169), which is housed in a 1937 art deco building downtown. The property’s 65 rooms are outfitted with sustainable wooden furniture and carpets made from recycled fibers, while three of the five 720-square-foot master suites (from $229) have whirlpools and fireplaces.
Step back in time at the Pfister (from $199), a Romanesque Revival building erected in 1893 and decked out with marble staircases, brass chandeliers, gilded ceilings, and the largest Victorian art collection of any hotel in the world. Upstairs, rooms are divided between the historic section, which was renovated less than three years ago, and a circular tower added in 1963 with direct views of Lake Michigan from the suites ending in 09.