Search for Cheap Deals on
Hotels with Pools in Chicago

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking, and you save up to 60%!


Featured Chicago Hotels with a Pool

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
3 out of 5
777 East Grand Avenue, Bensenville, IL
Fully refundableReserve now, pay when you stay
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5
221 N Columbus Dr, Chicago, IL
Fully refundable
Stay at this 4.5-star luxury hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast. Our guests praise the pool and the restaurant in our ...
Radisson Blu Aqua Hotel Chicago
InterContinental Chicago Magnificent Mile, an IHG Hotel
InterContinental Chicago Magnificent Mile, an IHG Hotel
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
Stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
InterContinental Chicago Magnificent Mile, an IHG Hotel
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Chicago. Enjoy 2 bars/lounges, breakfast, and WiFi. Our guests praise the restaurant and the helpful staff in our reviews. ...
Swissotel - Chicago
Holiday Inn Chicago - Schaumburg, an IHG Hotel
Holiday Inn Chicago - Schaumburg, an IHG Hotel
3.5 out of 5
1998 North Roselle Road, Schaumburg, IL
Fully refundable
Stay at this 3.5-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast. Popular attractions Woodfield Mall and LEGOLAND® Discovery ...
Holiday Inn Chicago - Schaumburg, an IHG Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4 out of 5
300 E Ohio St, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast. Our guests praise the pool and the restaurant in our ...
DoubleTree by Hilton Chicago - Magnificent Mile
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour health club. Our guests praise the breakfast and the helpful staff in our ...
Palmer House a Hilton Hotel
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
Stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast, and a health club. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Hilton Chicago
Country Inn & Suites by Radisson, Schaumburg, IL
Country Inn & Suites by Radisson, Schaumburg, IL
3 out of 5
1401 North Roselle Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
Stay at this family-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Country Inn & Suites by Radisson, Schaumburg, IL
Holiday Inn Chicago North Shore, an IHG Hotel
Holiday Inn Chicago North Shore, an IHG Hotel
3 out of 5
5300 West Touhy Ave, Skokie, IL
Fully refundable
Stay at this 3-star business-friendly hotel in Skokie. Enjoy free WiFi, free parking, and breakfast. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Chicago North Shore, an IHG Hotel
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Hilton Chicago/Oak Brook Hills Resort & Conference Center
4 out of 5
3500 Midwest Road, Oak Brook, IL
Fully refundableReserve now, pay when you stay
Stay at this spa hotel in Oak Brook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Hilton Chicago/Oak Brook Hills Resort & Conference Center
Four Points by Sheraton Chicago Schaumburg
Four Points by Sheraton Chicago Schaumburg
3 out of 5
1100 East Higgins Road, Schaumburg, IL
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast. Our guests praise the clean rooms in our reviews. Popular ...
Four Points by Sheraton Chicago Schaumburg