WALDORF ASTORIA CHICAGO The elegant Gold Coast Hotel houses the cushy Elysian Spa and Health Club. Try a water class in the lap pool, which is adorned with mosaic tiles. And if you forget your swimsuit, no worries: the hotel is a stone's throw from Bloomingdale's, Barneys, and a plethora of other shops. Rates start at $345 a night.
Photo credit: John Russo
FOUR SEASONS HOTEL CHICAGO The luxury hotel (do you sense a theme, here?) boasts a 50-foot long pool with subtle decor. Just kidding. There are Roman columns and a dramatic, domed glass ceiling. Rates start at $308 a night.
THE PENINSULA CHICAGO The Peninsula's indoor pool is surrounded with 20-foot windows that look out over the Mag Mile. Order up bites from the spa menu—we're talking cream-less tomato soup and a vegan afternoon tea— then sink into the striped sun chairs and keep pretending it's summer. Rates start at $399 a night.
TRUMP INTERNATIONAL HOTEL AND TOWER CHICAGO Grand even by Trump Standards, the heated indoor pool is 75-feet long. If you really want to live it up, book one of the Spa guestrooms, which offer direct access to the spa, health club, and pool. Better yet: they come stocked with heated neck and eye pillows. Rates start at $356 a night.
[Top Photo: HotelChatter, All Others Courtesy of The Hotels]