Title: Book the Best Hotels with POOL in Kenwood in 2026 | Expedia.ca [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)[Kenwood Car Rentals](https://expedia.ca/Car-Rentals-In-Kenwood.d6132343.Car-Rental-Guide)[Kenwood Vacations](https://expedia.ca/Kenwood.d6132343.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/829/94662344-53ef-4f49-b2be-cb6f7f2e4498.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/829/94662344-53ef-4f49-b2be-cb6f7f2e4498.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Kenwood Hotels with a Pool Tonight [Mar 13 - Mar 14](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2026-03-13&endDate=2026-03-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 14 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2026-03-14&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Kenwood hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a0ababda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/833194a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/58afb443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3,902 reviews) CA $141 CA $166 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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/f26e0a61.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/eea57c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) Downtown Chicago 8.4/10 Very good (1,714 reviews) - Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline. CA $176 CA $206 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/cff11fef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/82978823.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/1e5dfdc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/19300/19215/w3995h2662x0y0-e8059ef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Renaissance Chicago Downtown Hotel [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-Downtown-Hotel.h19215.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,002 reviews) - Splash into pure relaxation at this downtown hotel's indoor pool with loungers and fitness centre access. CA $260 CA $347 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-Downtown-Hotel.h19215.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) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.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) ![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/693d9c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) Downtown Chicago 8.6/10 Excellent (3,130 reviews) - Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match. CA $147 CA $173 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Outdoor 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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/af50ca75.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) ### DoubleTree by Hilton Chicago - Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) Downtown Chicago 8.8/10 Excellent (2,347 reviews) - Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile. CA $144 CA $169 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.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) ![Exterior](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/w1101h1283x0y1-ef09926c.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) ![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) ### The Hoxton Chicago [](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,001 reviews) - Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat. CA $185 CA $258 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information) ![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/fd4d7555.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/w2880h1919x0y0-e734d585.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) ![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) ### Radisson Blu Aqua Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information) Downtown Chicago 8.6/10 Excellent (1,865 reviews) - Luxurious indoor and seasonal outdoor pools form a relaxing oasis near Millennium Park and Michigan Avenue. CA $215 CA $288 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.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) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/83e4c147.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) ![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) ### JW Marriott Chicago [](https://www.expedia.ca/Chicago-Hotels-JW-Marriott-Chicago.h3538327.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,000 reviews) - Sleek indoor pool sanctuary opens onto Chicago adventures in this luxury retreat. CA $271 CA $367 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Chicago-Hotels-JW-Marriott-Chicago.h3538327.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/58291697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/83f39cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ccaab668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/77000000/76270000/76267500/76267438/ecc0a878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sentral Michigan Avenue [](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,104 reviews) - Indoor pool oasis at upscale Michigan Avenue aparthotel offers year-round swimming enjoyment. CA $161 CA $229 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Chicago-Hotels-Sentral-Michigan-Avenue.h76267438.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown South Loop [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1,898 reviews) - Dive into downtown luxury with a rejuvenating pool experience close to Chicago landmarks. CA $161 CA $189 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.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=2026-03-27&endDate=2026-03-28®ionId=6132343&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Kenwood Breakfast included 4 stars 5 stars Hot tub Spa ## Top Kenwood Hotel Reviews ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Alrighty" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg) ### Congress Plaza Hotel 4/10 Poor "The hotel is very dated. Room had stale smell. Staff brought us extra sheets and fans to keep the room cooler. The staff what there is was helpful. No one really is around." [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/fa2dd97c_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Our stay at this property was AMAZING!! The whole staff was polite and attentive! The hotel itself was very clean and organized! Not to mention the view we had in our room... BEAUTIFUL!! Would definitely book here again, 10/10 recommend for your next chicago trip" [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Great location. Good amenities. Nice breakfast. Comfy beds. Quiet." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b_y.jpg) ### Swissotel - Chicago 6/10 Okay "Outdated property for the price" [](https://expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "Friendly staff" [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg) ### The Wade 10/10 Excellent "Walking distance to most of what we wanted to see. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7705f099_y.jpg) ### Courtyard by Marriott Chicago Magnificent Mile 10/10 Excellent "Clean room, staff was friendly! Fridge in room, microwave in market. We didn’t park a car but it was $60-$75 a night. Located walking distance to everything we wanted to go do. Deposit of $70 a night. They also provide umbrellas for a $20 hold. " [](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Clean rooms, great staff, great amenities. Next to the loop and the red line. In the heart of downtown Chicago, very historic and beautiful. " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Kenwood? ### What is there to see and do in Kenwood? ### When is the best time to book a hotel with a pool in Kenwood? ## 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) - [Luxury Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [B&B in Chicago 47th Street Station ](https://www.expedia.ca/Chicago-47th-Street-Station-Bed-And-Breakfast.d6212783-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hotels near Chicago 47th Street Station ](https://www.expedia.ca/Chicago-47th-Street-Station-Hotels.d6212783.Travel-Guide-Hotels) - [Guest Houses in Chicago 51st-53rd Street Station ](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Guest-Houses.d6212787-aaGuestHouses.Travel-Guide-Accommodation) - 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