The Drake Hotel

A traditional "old money" stomping ground favored by Chicago socialites and celebrities, this stately icon exudes old-school style, with velvet seats in elevators, bowls of fresh fruit lining the check-in desk and enormous chandeliers. Feels a bit like crashing a rich aunt’s downtown condo, yet some parts of the hotel are a bit tired. *High-speed Internet (free wireless in public spaces for guests using Internet in rooms and $6.95/hr for nonusers; $12.95–$16.95 via cable in rooms).