Title: Book the Best Hotels with POOL in Hillside in 2026 | Expedia.ca [Hotels in Hillside](https://expedia.ca/Hillside-Hotels.d8353.Travel-Guide-Hotels)[Vacation Rentals in Hillside](https://expedia.ca/Hillside-Vacation-Rentals.d8353.Travel-Guide-VacationRentals)[Flights to Hillside](https://expedia.ca/Cheap-Flights-To-Hillside.d8353.Travel-Guide-Flights)[Hillside Car Rentals](https://expedia.ca/Car-Rentals-In-Hillside.d8353.Car-Rental-Guide)[Hillside Vacation Packages](https://expedia.ca/Hillside.d8353.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/8353/04417658-847c-4a59-a291-8bfe14a93297.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Off The Beaten Track ![](https://images.trvl-media.com/place/8353/04417658-847c-4a59-a291-8bfe14a93297.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 Hillside Hotels with a Pool Tonight [Apr 1 - Apr 2](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-04-01&endDate=2026-04-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 2 - Apr 3](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-04-02&endDate=2026-04-03&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=8353&startDate=2026-04-10&endDate=2026-04-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Hillside hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2370000/2363600/2363526/a6cedb2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free continental breakfast on weekdays](https://images.trvl-media.com/lodging/3000000/2370000/2363600/2363526/ce7f9d13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2370000/2363600/2363526/427c64bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2370000/2363600/2363526/bac7cd7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Chicago West - O'Hare Arpt Area by IHG [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-West-Ohare-Arpt.h2363526.Hotel-Information) Hillside 7.0/10 Good (1,000 reviews) "Great location, stores at walking distance and restaurants too. 20 min from the Airport!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ivon Marlen CA $141 CA $157 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-West-Ohare-Arpt.h2363526.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) ![Banquet hall](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/2ad62276.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 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) Downtown Chicago 8.6/10 Excellent (3,151 reviews) "Nice location and good hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taneshia CA $146 CA $171 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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/w3995h2662x0y0-e8059ef2.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) ### Renaissance Chicago Downtown Hotel [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-Downtown-Hotel.h19215.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,001 reviews) "Clean Room, Friendly and attentive staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Felix CA $291 CA $383 total includes taxes & fees Apr 4 - Apr 5 [](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-Downtown-Hotel.h19215.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 (2,387 reviews) "Loved this hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen CA $152 CA $179 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/1c7b677d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/832f7b8b.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,348 reviews) "Beautiful property, great resturant on site, an the pool and spa was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $256 CA $335 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/290000/281600/281523/edec057f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/290000/281600/281523/ec36b84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/290000/281600/281523/641753df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/290000/281600/281523/a6616a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Chicago-Downtown [](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown.h281523.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1,159 reviews) "Great stafff great breakfast great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $170 CA $200 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown.h281523.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) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/dec7b24e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d288265e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) Downtown Chicago 8.6/10 Excellent (4,421 reviews) "Clean rooms, great location, staff as friendly and attentive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin CA $170 CA $200 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.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) ![Lobby](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/459a3527.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) ![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) ### JW Marriott Chicago [](https://www.expedia.ca/Chicago-Hotels-JW-Marriott-Chicago.h3538327.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,004 reviews) "Hot tubs was the best part!! Super hot water " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Myeisha CA $319 CA $423 total includes taxes & fees Apr 4 - Apr 5 [](https://www.expedia.ca/Chicago-Hotels-JW-Marriott-Chicago.h3538327.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/b76bffdb.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) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/6234383e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/3a5d3e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Chicago Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,073 reviews) "Clean room, very new, excellent stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $200 CA $276 total includes taxes & fees Apr 7 - Apr 8 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/92caac39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7c24871d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7705f099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/a2db9cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Chicago Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,828 reviews) "The location and the hotel was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan CA $174 CA $204 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.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=2026-04-15&endDate=2026-04-16®ionId=8353&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Hillside Breakfast included Hot tub 4 stars 5 stars Spa ## Top Hillside Hotel Reviews ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg) ### Hilton Chicago O'Hare Airport 10/10 Excellent "The hotel environment is very nice. Clean room，friendly staff " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg) ### Hotel Felix River North/Magnificent Mile 8/10 Good "The bar was fine we got 2 free drinks." [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "sleeper sofa to old. Super Uncomfortable " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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 "GOOD BREAKFAST, THE ROOM WAS CLEAN. THANK YOU." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "The staff were excellent. The hotel was very clean and the location was perfect." [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/3cb3732b_y.jpg) ### Swissotel - Chicago 10/10 Excellent "Beautiful hotel. Large, nice room with a nice view. I would love to stay here again. Highly recommend. " [](https://expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg) ### The Wade 8/10 Good "Lake/Beach view was great, we were switched rooms, our room was not yet cleaned yet" [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.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 "No food amenities at all. " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.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 "Everything was great about the breakfast except the hostess that seated me. Everyone else at the hotel was friendly but she seemed to be put out seating me. She was on her phone at the front stand the entire breakfast after begrudgingly seating me while all the other staff was friendly and accommodating. Almost made me not want to go back." [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Hillside? ### What is there to see and do in Hillside? ### When is the best time to book a hotel with a pool in Hillside? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Vacation Rental - More ways to book - [Farmstay in Bellwood ](https://www.expedia.ca/Bellwood-Agritourism.d6132079-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Bellwood ](https://www.expedia.ca/Bellwood-Bed-And-Breakfast.d6132079-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Golf Hotels in Bellwood ](https://www.expedia.ca/Bellwood-Hotels-Golf-Hotel.0-0-d6132079-tGolfHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Bellwood ](https://www.expedia.ca/Bellwood-Hotels-Spa-Hotel.0-0-d6132079-tSpaHotel.Travel-Guide-Filter-Hotels) - [Bellwood Hotels ](https://www.expedia.ca/Bellwood-Hotels.d6132079.Travel-Guide-Hotels) - 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