Title: TOP Hotels with Pools in South Side, IL for 2026 - South Side Hotels with a Pool | Expedia.co.uk [South Side Travel Guide](https://expedia.co.uk/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Holiday Rentals in South Side](https://expedia.co.uk/South-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals)[Flights to South Side](https://expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide)[South Side Holidays](https://expedia.co.uk/South-Side.d553248635074842823.Holidays-City-Breaks) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 Pool Tonight [15 Mar - 16 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-15&endDate=2026-03-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [16 Mar - 17 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-16&endDate=2026-03-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [20 Mar - 22 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [27 Mar - 29 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-27&endDate=2026-03-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for 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) ![Serves lunch, dinner and happy hour](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/573f8c28.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/1000000/900000/892200/892168/2fd33e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves lunch, dinner and happy hour](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/7cf4bf83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Marriott Midway [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) Bedford Park 8.4/10 Very good (925 reviews) "Great service, friendly staff. Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adrian £114 includes taxes & fees 19 Mar - 20 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/w2551h3837x3y3-626dfd55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/fb6e2600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,677 reviews) "Amazing place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nia £138 includes taxes & fees 1 Apr - 2 Apr [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.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 duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room service – dining](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade [](https://www.expedia.co.uk/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) Downtown Chicago 8.4/10 Very good (1,721 reviews) "Walking distance to most of what we wanted to see. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tabitha £114 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/c95917cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/1f085992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/459a3527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### JW Marriott Chicago [](https://www.expedia.co.uk/Chicago-Hotels-JW-Marriott-Chicago.h3538327.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,000 reviews) "Room was great, the staff and concierge exceeded expectations!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marlon £210 includes taxes & fees 27 Mar - 28 Mar [](https://www.expedia.co.uk/Chicago-Hotels-JW-Marriott-Chicago.h3538327.Hotel-Information) ![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) ![2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/8d2143ec.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) ![3 bars/lounges, piano bar](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/f598823d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hoxton Chicago [](https://www.expedia.co.uk/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,002 reviews) "Room was very clean and comfortable. Food at the hotel is a bit pricey but good. Very well located close to restaurants, bars and shops " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim Z. £141 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/e065e04c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/3b2677cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/5bee96cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown South Loop [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1,908 reviews) "Staff was friendly, valet parking is quick and the attached restaurant is very good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Codi £105 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) ![Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/fd4d7555.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/d70c748e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/44865590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Radisson Blu Aqua Hotel Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information) Downtown Chicago 8.6/10 Excellent (1,869 reviews) "Overall a great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua £151 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.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) ![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/ec33d4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/be69fa71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/0ea4e737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile [](https://www.expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) Downtown Chicago 8.2/10 Very good (2,801 reviews) "Every thing was in walking distance and the hotel is beautiful I will definitely be back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannon £123 includes taxes & fees 22 Mar - 23 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Outdoor pool, pool cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/a08c52fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/6b5099c2.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) ![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 [](https://www.expedia.co.uk/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) Downtown Chicago 8.8/10 Excellent (2,355 reviews) "Loved this hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen £94 includes taxes & fees 22 Mar - 23 Mar [](https://www.expedia.co.uk/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.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) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4a14c915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/066ab9a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, Netflix, pay films, streaming services](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/cccba568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Grand Chicago Riverwalk [](https://www.expedia.co.uk/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.Hotel-Information) Downtown Chicago 8.6/10 Excellent (1,619 reviews) "Hotel was clean, staff was friendly. Only downside is breakfast is buffet only." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caitlin £192 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.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.co.uk/Hotel-Search?startDate=2026-03-29&endDate=2026-03-30®ionId=553248635074842823&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in South Side Breakfast included 4 stars 5 stars Hot tub Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_SPRING_PROMO_553248635074842823) ## Top South Side Hotel Reviews ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg) ### Holiday Inn Chicago – Midway Airport S by IHG 8/10 Good "Room was nice but need internet in the tv so you can log into your own streaming services. " [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/099e5443_y.jpg) ### Chinatown Hotel Chicago 6/10 Okay "It was very cold in the room. The air conditioning definitely works! The water in the shower was very warm and nice. The bed could use a thicker comforter or at least an extra blanket. Overall, I don’t know what I expected given the price." [](https://expedia.co.uk/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 "The staff members were all very accommodating and friendly. The room was clean and the bed was comfortable. The area had lots of restaurants within walking distance and it was an easy drive to the hospital where my son was admitted. " [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.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 "The staff was very nice and housekeeping was great! We had everything we needed and had no issues. " [](https://expedia.co.uk/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Chicago Lake Shore Hotel](https://images.trvl-media.com/lodging/1000000/10000/7400/7341/5dc5b9fc_y.jpg) ### Chicago Lake Shore Hotel 4/10 Poor "Amenities are nothing like what was shown on Expedia. The entire complex appears to have been abandon or is the process of being abandoned. I saw several rooms on the property that appeared to have been half-way in construction attached to properties that appeared to have been abandoned. The room gives you cups and an ice container but there are no ice-machines on the property. Rooms were just okay, nothing impressive. Lighting could be better. Television systems had poor reception and couldn’t use chrome cast despite the TV’s own function. Property could stand to be more upfront of its current status of development." [](https://expedia.co.uk/Chicago-Hotels-Chicago-Lake-Shore-Hotel.h7341.Hotel-Information) ![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/7cf4bf83_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "I didn't have an airport shuttle. I was a little difficult to distinguish between the two properties. Breakfast was inexpensive but realky should have come with the room expense. The bar and bartender were warm and welcoming. The restaurant at night looked closed and uninviting. All in all no complaints. 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