Title: Book the Best Hotels with POOL in Countryside in 2025 | Expedia.ca [Hotels in Countryside](https://expedia.ca/Countryside-Hotels.d7682.Travel-Guide-Hotels)[Vacation Rentals in Countryside](https://expedia.ca/Countryside-Vacation-Rentals.d7682.Travel-Guide-VacationRentals)[Things to do in Countryside](https://expedia.ca/Things-To-Do-In-Countryside.d7682.Travel-Guide-Activities)[Countryside Car Rentals](https://expedia.ca/Car-Rentals-In-Countryside.d7682.Car-Rental-Guide)[Countryside Vacation Packages](https://expedia.ca/Countryside.d7682.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/c35c218970c350807ee142ef01d2690b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Monica Ferro # Find Hotels with a Pool in Countryside, IL from CA $207 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Countryside Hotels with a Pool Tonight [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=7682&startDate=2025-10-04&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=7682&startDate=2025-10-05&endDate=2025-10-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7682&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7682&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Countryside Hotels with a Pool ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/52469d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, piano bar](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/d06b01bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/9752c1a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/w1101h1283x0y1-ef09926c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hoxton Chicago Downtown Chicago 9.0/10 Wonderful (1001) "Beautiful hotel in a great location " CA $306 CA $359 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/feb0b94d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/1bc6749f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view from property](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/d1cc0289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/7b0fa7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Chicago West Loop Downtown Chicago 8.8/10 Excellent (1045) "Great location near lots of restaurants. " CA $271 CA $318 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information) ![Executive lounge](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Suite | Living area](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/54bf755e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/4df733bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Suite](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/w4238h2832x0y0-ef315dd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Level Chicago Fulton Market Downtown Chicago 9.2/10 Wonderful (312) "Great place will return " CA $264 CA $341 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-Level-Chicago-Fulton-Market.h95823687.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Chicago - Magnificent Mile Downtown Chicago 8.8/10 Excellent (2076) "Great hotel" CA $222 CA $261 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (1996) "Great property with great staff and amenities. " CA $245 CA $323 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/2d5c8626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/2e2df9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/0667db43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/9b501315.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Chicago Downtown South Loop Downtown Chicago 8.8/10 Excellent (2056) "Beautiful place loved everything about this hotel" CA $224 CA $263 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-South-Loop.h33387384.Hotel-Information) ![Indoor pool, open 7:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2844) "Had a great stay!" CA $201 CA $236 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Seasonal outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/cb208a99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Single Bed, City View | Living area](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/f7ca0ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/9bdb478c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Level Chicago – Old Town Downtown Chicago 9.0/10 Wonderful (361) "Great place to stay. Loved it!" CA $224 CA $294 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-LEVEL-Furnished-Living-Chicago.h39805843.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/520a670b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f7f78ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/b6152ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 2 Double Beds, Non Smoking, Refrigerator (with Sofabed)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/aeb6fede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western River North Hotel Downtown Chicago 7.8/10 Good (1017) "Great stay" CA $177 CA $207 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1faa6c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/896a6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown River North Downtown Chicago 8.6/10 Excellent (5029) "Overall a great stay - will be saying this place for future - Thanks" CA $243 CA $285 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19®ionId=7682&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Countryside Hotel Reviews ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Overall a great stay - will be saying this place for future - Thanks" [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Everything was awesome. Location is excellent, shopping is nearby with plenty of restaurants. The complementary buffet breakfast is delicious." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "Dude this place was awesome the view was amazing it’s right in front of O beach, we stayed here for lollapalooza and it was a walking distance and so affordable. There’s a beautiful bar in the lobby that you can drink at and also during festivals they have pop up activations with giveaways such as aperol spritz. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Top Lage, sehr zentral" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Perfect location, in walking distance to Michigan Ave, Millennium Park, Navy Pier. Friendly staff, easy check in. " [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Great location to and walking to riverwalk, millennium park. Metro is right outside the front door. " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Clean rooms, great staff, everything in walking distance from hotel. Would stay here again. " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "someone smoked as the mattress smelled of smoke. luggage rack is broken" [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Outstanding place to stay in downtown Chicago " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Countryside? > [Congress Plaza Hotel](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information): Hotel, 4-minute walk from Michigan Avenue. Provides complimentary wired internet access, an indoor pool, and LCD televisions. [Hilton Chicago/Magnificent Mile Suites](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information): Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a steam room. [Hilton Garden Inn Chicago Downtown/Magnificent Mile](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information): Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. [Hilton Chicago O'Hare Airport](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information): Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions. [CitizenM Chicago Downtown](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information): Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool, and a health club. ### What is there to see and do in Countryside? > Explore places like Michigan Avenue, Navy Pier, and Wrigley Field while you're in the area. Enjoy a stroll along the shore at Centennial Beach and Oak Street Beach. Travelers love Countryside for its array of dining options. ### When is the best time to book a hotel with a pool in Countryside? > You may want to consider a place to stay that has an outdoor pool if you're planning to visit Countryside in the hottest months of July, August, or June when the average temp is 71°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 31°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Adults Only Resorts & in Bedford Park](https://www.expedia.ca/Bedford-Park-Chicago-Hotels-Adults-Only-Resorts.0-n7224-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Bedford Park](https://www.expedia.ca/Bedford-Park-Chicago-Hotels-Cheap-Hotels.0-n7224-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Bedford Park](https://www.expedia.ca/Bedford-Park-Chicago-Hotels-Hotels-With-Childcare.0-n7224-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bedford Park](https://www.expedia.ca/Bedford-Park-Chicago-Hotels-Luxury-Hotel.0-n7224-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Burr Ridge](https://www.expedia.ca/Burr-Ridge-Hotels-Business-Hotel.0-0-d6330-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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