The best hotel pools in Chicago provide travelers with something to think about when searching for their Windy City accommodations. Having a pool oasis to retreat to can be a great thing when a break from exploring the city is in order, for example, and depending on the pool in question, it might be available for swim-based workouts. Of course, nobody will fault you if you choose relaxation over working out while spending time at your Chicago hotel pool of choice. Either way, the fact that you have a pool at your disposal can only add extra depth to your Chicago vacation.

Downtown Chicago Hotels with Outdoor Pools

Many of the best Chicago hotels with pools are found in the downtown Loop area. Examples include several hotels along the famous Miracle Mile. Standouts in particular include the Peninsula and the Four Seasons. The Peninsula pool is a heated indoor pool that is complemented by an outdoor sun deck that overlooks the city. At the Four Seasons, the indoor pool area is an elegant oasis that is crowned by a skylight. A number of other hotels in the Miracle Mile area also offer swimming pools for those who wish to expand their options. At the InterContinental Chicago, for example, a wonderfully ornate indoor pool area is available for guests to take advantage of, and the Hyatt Chicago Magnificent Mile counts a stylish indoor pool among its various facilities. Off the Miracle Mile, but also in the downtown area, is the Radisson Blu Aqua Hotel, which boasts a seasonal outdoor pool to go with its indoor pool.

Another part of the city that is worth focusing on when trying to find Chicago hotels with pools is the Near North Side area, which is essentially an extension of the downtown area. In the River North neighborhood of the Near North Side, for example, the lofty Trump International Hotel & Tower features a 75-foot by 25-foot heated indoor pool with amazing city views. Other River North hotels that deserve mention among the best Chicago hotels with pools are the Hilton Garden Inn and the Hotel Palomar. For more ideas, head to the South Loop area of downtown Chicago, where such hotels as the Essex Inn and the Hilton offer some of the best hotel pools in Chicago.

Chicago Map

Chicago Rooftop Pools

The Chicago skyline is a joy to admire, and there are plenty of different vantage points from which to do so. Among these vantage points are the city’s rooftop pools. An example of one such pool would be the rooftop pool at the aforementioned Hotel Palomar. This is a heated indoor pool, and it is complemented by a sundeck. Also noted before was the Essex Inn in the South Loop area. Its dynamic indoor pool area is on the fourth floor and offers splendid views of Lake Michigan. Back up in the Near North Side area is the W Chicago Lakeshore. Among this hotel’s impressive amenities is a hip indoor pool with an outdoor rooftop terrace.

Being that the weather in Chicago can be cold and unpredictable, outdoor pools are relatively few and far between. As such, rooftop pools that aren’t enclosed are also scarce. At the Crowne Plaza Magnificent Mile, however, a wonderful rooftop pool with an open roof awaits. Surrounding this outdoor pool, it should be noted, are floor-to-ceiling windows that allow guests to enjoy scintillating city views.