Title: Book the Best Hotels with POOL in Near South Side in 2026 | Expedia.ca [Near South Side Travel Guide](https://expedia.ca/Chicago-Near-South-Side.dx6132399)[Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Near South Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-South-Side.d6132399.Car-Rental-Guide)[Near South Side Vacations](https://expedia.ca/Near-South-Side.d6132399.Destination-Travel-Guides) ![Chicago_NearSouthSide_6132399_05](https://images.trvl-media.com/place/6132399/d6571aed-ec1a-4cde-82c6-09026eacaa3d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Near South Side, IL from CA $117 - ![](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 Near South Side Hotels with a Pool Tonight [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-12-01&endDate=2025-12-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-12-02&endDate=2025-12-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Near South Side Hotels with a Pool ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114548/3ba0dd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114548/39f1f0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114548/5570a0c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114548/bb16643e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Chicago McCormick Place Near South Side 9.2/10 Wonderful (721) "Clean room, great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine CA $100 CA $117 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Chicago-Hotels-Home2-Suites-By-Hilton-Chicago-McCormick-Place.h20114548.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114575/eed61302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114575/51f5e8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114575/68735b07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20120000/20114600/20114575/7b214ea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago McCormick Place Near South Side 8.6/10 Excellent (1009) "Hotel is very close to restaurant. Rooms are nice and clean. Rooftop bar is also nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yolanda CA $105 CA $123 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-McCormick-Place.h20114575.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251274/84e2750c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251274/3f88d3c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251274/70f56d62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251274/5c2508de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Chicago McCormick Place Near South Side 9.0/10 Wonderful (1023) "Everything was Wonderful great hotel great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shena CA $111 CA $130 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-McCormick-Place.h23251274.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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/ddbd86a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG Downtown Chicago 8.8/10 Excellent (3418) "Great hotel!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deja CA $133 CA $156 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/cc17dca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/03795c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Accessible (Roll-In Shower)](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/7e320684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/3ee5bb80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Chicago Medical District UIC Near West Side 9.6/10 Exceptional (352) "Would stay there again...loved it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $122 CA $143 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Suites-Chicago-Medical-District-Uic.h102236658.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.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) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (2119) "Great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron CA $149 CA $210 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/f36e2ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/128dfde4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/18c5ca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile Downtown Chicago 8.4/10 Very good (4225) "Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rodger CA $114 CA $134 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.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) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2957) "Great location, the staff was friendly and the room was very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Breanna CA $126 CA $148 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (The Artist Suite)](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/0144d6ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/d3f07aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/e1eb307d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Royal Sonesta Chicago River North Downtown Chicago 9.2/10 Wonderful (2292) "Great place - stayed with extended family. Lounge areas and amenities met everyone’s needs " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $143 CA $213 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.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) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1faa6c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.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 (5352) "Nice staff A lot of restaurants and stores near the hotel Good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Viviana Velazquez CA $129 CA $151 total includes taxes & fees Dec 7 - Dec 8 [](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=2025-12-15&endDate=2025-12-16®ionId=6132399&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Near South Side Hotel Reviews ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "We had a great stay and will be back again." [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Location, view, and service were all fantastic " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg) ### Club Quarters Hotel Wacker at Michigan, Chicago 10/10 Excellent "A good place for stay " [](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Staff and amenities. Room service. " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Very nice hotel " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Very efficient checkin and courtesy of staff was excellent " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Clean room" [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Absolutely gorgeous! This hotel offers everything you need and want. Excellent food, amenities and the spa is the best part. We had a mother and daughter weekend with massage's, it was what we hoped for and more. " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Nice staff & clean room" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Near South Side? > [Palmer House a Hilton Hotel](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information): Hotel steps from State Street. Features a full-service spa, an indoor pool, and a 24-hour fitness center. [Embassy Suites by Hilton Chicago Downtown River North](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information): Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool, and flat-screen 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 sauna. [Congress Plaza Hotel](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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 Near South Side? > Explore places like Soldier Field and Lake Michigan while you're in Near South Side. Surround yourself with nature at Burnham Park and Grant Park. Travelers love Near South Side for its array of dining options. ### When is the best time to book a hotel with a pool in Near South Side? > You may want to consider an accommodation with an outdoor swimming pool if you'll be visiting in the warmest months of July, August, or June when the average temperature is 70°F. 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