Find Hotels with a Pool in Chicago, IL from CA $254

Loews Chicago Hotel is a fantastic choice for travellers seeking a blend of luxury and convenience, featuring a stunning outdoor pool complemented by a poolside bar where you can unwind with a refreshing drink. Rated 9.4 by guests, this 4.5-star hotel is known for its friendly and helpful staff, as well as its comfortable and clean rooms. With views of the river and easy access to the shopping district, it's an ideal spot for families looking to explore the city while enjoying top amenities.Another excellent option is the Viceroy Chicago, also rated 9.4, offering a chic outdoor pool experience with sun loungers for relaxing afternoons. Guests rave about the beautiful and clean rooms, and the staff's excellent service makes every stay feel special. Conveniently located in a vibrant shopping district, this 4.5-star hotel combines comfort with style, making it superb for those who want both adventure and relaxation.For those in search of an upscale experience, Nobu Hotel Chicago stands out with its luxurious outdoor pool and impeccable service. With a superb rating of 9.4, this 5-star hotel provides guests with premium amenities, including deep soaking bathtubs and designer toiletries. The friendly staff and fantastic room quality ensure a memorable stay, making it ideal for families looking to indulge during their trip.Kasa River North Chicago, rated 9.6, offers a more casual yet equally appealing option with its rooftop terrace and outdoor pool. Families will appreciate the well-equipped kitchen facilities and free Wi-Fi, superb for those who enjoy a cozy feel while traveling. The friendly front desk staff and fantastic amenities further enhance the overall experience.Lastly, the Hampton Inn & Suites Chicago Downtown, with a rating of 9.2, provides a budget-friendly option featuring a warm outdoor pool and complimentary breakfast. Families will love the spacious rooms and the welcoming atmosphere, making it a great choice for a fun-filled Chicago getaway.Each of these hotels not only offers outdoor pools but also a range of amenities that cater to families and adventurous travellers alike.

The Loews Chicago Hotel is a fantastic option for travellers seeking an outdoor pool with stunning scenic views. This 4.5-star hotel not only offers a refreshing poolside bar for leisurely afternoons but also features breathtaking river and lake views that guests rave about. With a remarkable traveller rating of 9.4, visitors frequently praise the friendly and helpful staff, the comfortable and clean rooms, and the overall excellent service.Another great choice is the Viceroy Chicago, also rated at 4.5 stars and boasting a beautiful outdoor pool area. Guests enjoy lounging on the sun loungers while soaking in picturesque lake views. With a traveller score of 9.4, it's no surprise that many reviews highlight the hotel's great location and the excellent quality of service provided by the friendly staff.For those who prefer a central location, the Renaissance Chicago Downtown Hotel offers an inviting outdoor pool with lovely river views. This 4-star hotel holds a solid traveller rating of 9.2, with many guests praising the helpful staff and the quality of food and drinks available on-site.Finally, The Ritz-Carlton, Chicago stands out as a luxurious 5-star option, featuring an outdoor pool with captivating lake views that guests find exceptional. With a traveller rating of 9.2, this hotel is known for its beautiful rooms and outstanding service, making it a worthy choice for a memorable stay.

The DoubleTree by Hilton Chicago - Magnificent Mile is a fantastic choice for travellers seeking an outdoor oasis in the heart of the city. With a rating of 8.8 from guests, this 4-star hotel features a delightful outdoor pool equipped with cabanas, sun loungers, and a poolside bar, making it an ideal spot for relaxation after a day of exploring. Guests rave about the hotel's friendly staff and the cleanliness of the rooms, which enhances the overall experience.For those looking for a family-friendly option, the Holiday Inn Express & Suites Chicago Schaumburg by IHG also shines with its outdoor pool that includes free cabanas and sun loungers. Rated 9.0 by travellers, this hotel offers a spacious and convenient stay, complemented by a complimentary buffet breakfast that is both delicious and satisfying.The Radisson Blu Aqua Hotel Chicago offers a touch of luxury with its resort-style outdoor pool, complete with free cabanas and sun loungers. Guests appreciate the beautiful and clean rooms, along with exceptional service, earning the hotel a great rating of 8.6.Lastly, families can enjoy a fun-filled stay at the Great Wolf Lodge Illinois, which features both indoor and outdoor pools, along with cabanas. With a rating of 8.6, this hotel is well-loved for its clean rooms and amazing water park, ensuring that everyone in the family has a blast.

The DoubleTree by Hilton Chicago Midway Airport is a fantastic choice for travellers seeking comfort and convenience near the airport, just 1.1 miles away from Chicago, IL (MDW-Midway Intl.). This 4-star hotel not only has an inviting space with its friendly staff but also features a delightful outdoor pool where families can unwind and soak up the sun.In addition to the inviting pool area, you'll find plenty of amenities designed to enhance your stay. Guests rave about the clean and spacious rooms, equipped with essentials such as free Wi-Fi and complimentary toiletries. Families traveling with young children will appreciate the availability of cribs at no extra charge, ensuring a straightforward experience.Moreover, the hotel provides a 24-hour airport shuttle service, making it incredibly convenient for those arriving or departing from the airport. Self-parking is also free, adding to the overall value of your stay.

The Loews Chicago Hotel is a fantastic choice for travellers seeking a refreshing poolside experience. This 4.5-star hotel boasts a poolside bar where guests can indulge in delicious food and drinks while enjoying the sun-drenched atmosphere. Rated 9.4 by visitors, it's praised for its friendly staff, comfortable rooms, and excellent service, making it a reliable option for travellers.Another great option is The Robey, Chicago, a Member of Design Hotels. With a traveller review score of 9.2, this 3.5-star hotel also features a poolside bar that enhances the overall experience for guests looking to relax by the water. Visitors love the beautiful, clean rooms and the attentive staff, ensuring that your time spent poolside is both enjoyable and convenient.Hilton Grand Vacations Club Chicago Magnificent Mile is yet another hotel to consider, offering a poolside bar alongside spacious rooms and convenient amenities. Guests appreciate the great location and friendly service here, contributing to its rating of 9.2.For a stylish, urban vibe, The Hoxton Chicago stands out with its poolside bar and a score of 9.0. This 4-star hotel not only provides a lively option but also features friendly staff and comfortable, super clean rooms, making it a delightful option for families wanting to unwind.Lastly, The Hotel at Midtown combines leisure with fitness, offering a poolside bar as well. This 4-star property, rated 9.0, is known for its beautiful rooms and fantastic amenities, ensuring that both relaxation and fun are on the agenda for your stay.