Find Hotels with an Outdoor Pool in Highland Hills, IL

Mediterranean flavors await poolside at this eco-certified Chicago hotel where the seasonal rooftop pool becomes a social hub by day and a sophisticated bar venue by night, complemented by free bicycle rentals for urban exploration.

Poolside loungers invite sun-soaked relaxation at this downtown Chicago retreat near Willis Tower. The seasonal outdoor pool complements the 24-hour health club, while premium bedding and deep soaking tubs await after city adventures.

Sparkling waters beckon within this resort's indoor pool sanctuary, complemented by a soothing hot tub for post-golf muscle relief. Guests appreciate the thoughtfully arranged sun loungers and umbrellas while enjoying convenient pool hours from 10:00 AM to 7:00 PM.

Seasonal poolside relaxation awaits at this upscale Chicago retreat, where the outdoor swimming area complements stylish accommodations featuring rainfall showers and deep soaking tubs. Savor stunning city views from beautifully decorated rooms.

Seasonal swimming delights await in the outdoor pool, open May through September for refreshing dips after exploring nearby hiking trails. This hotel earns praise for its peaceful atmosphere, spotless rooms, and attentive staff.

Poolside perfection awaits at this upscale Chicago retreat, where the seasonal swimming area complements fitness facilities and bike rentals. After splashing around, guests appreciate spacious rooms with full kitchens and premium bedding for total comfort.

Dive into either the refreshing indoor or sun-drenched outdoor pool at this upscale retreat. A 24-hour fitness center, on-site restaurant serving delicious meals, and meticulously clean rooms create a perfectly balanced getaway experience.

Sparkling indoor and outdoor pools create year-round swimming retreats at this O'Hare airport hotel. After refreshing dips, guests savor American cuisine at Brickton restaurant or unwind in spacious rooms with pillowtop mattresses.