Title: Book the Best Hotels with POOL in South Side in 2026 | Expedia.ca [South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides) ![I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck. ](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Remington # Find Hotels with a Pool in South Side, IL from CA $135 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on South Side Hotels with a Pool Tonight [Dec 8 - Dec 9](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-08&endDate=2025-12-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-09&endDate=2025-12-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/74dfee01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/be9d08c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/c7ca0628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/811c6f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Marriott Midway Bedford Park 8.4/10 Very good (909) "The property was excellent the rooms fantastic and the staff were equally wonderful and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leilani CA $178 CA $209 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/d85dc510.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/63edec8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/186b641d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Chicago Magnificent Mile Downtown Chicago 9.0/10 Wonderful (1048) "Great Hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy CA $135 CA $199 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.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/1000000/10000/8100/8079/8318473d.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 (2124) "Loved and enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luis CA $142 CA $201 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/311c65a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, Netflix, pay movies, streaming services](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/edeb1954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/247d9e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/e436fe11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Grand Chicago Riverwalk Downtown Chicago 8.4/10 Very good (1576) "Professional staff, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $206 CA $283 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.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) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.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) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2955) "Great location and great staff!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) lynne CA $115 CA $135 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Indoor pool, open 5:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/a8da386d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/dd081548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG Downtown Chicago 8.8/10 Excellent (3446) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clara CA $160 CA $188 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/66b60053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/481e5f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/9cc7a10c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Chicago Dwtn - The Mart by IHG Downtown Chicago 8.8/10 Excellent (2033) "Great hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mario CA $135 CA $159 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Chicago - Magnificent Mile Downtown Chicago 8.8/10 Excellent (2184) "Nice Hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan CA $124 CA $145 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/2435ca6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/db08811d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/71356b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile Downtown Chicago 8.2/10 Very good (2748) "Great food clean room friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARINA CA $116 CA $177 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/da99f4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6efd5146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/c042bdff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade Downtown Chicago 8.4/10 Very good (1509) "Great location, walkable to so many area attractions. Would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debbie CA $140 CA $164 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.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=2025-12-22&endDate=2025-12-23®ionId=553248635074842823&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Clean room, kind staff!" [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "Everything is great. Ill be staying here again in my next visit." [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Very convenient and clean and friendly! " [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "Hotel and room was very clean and the desk clerk was courteous " [](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Cheap Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Cheap-Hotels.0-n6132245-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Family-Hotel.0-n6132245-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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