Title: Book the Best Hotels with POOL in Highland Hills in 2025 | 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)[Highland Hills Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Hills.d6132236.Car-Rental-Guide)[Highland Hills Vacations](https://expedia.ca/Highland-Hills.d6132236.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Highland Hills, IL ![](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 Highland Hills Hotels with a Pool Tonight [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=6132236&startDate=2025-10-28&endDate=2025-10-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=6132236&startDate=2025-10-29&endDate=2025-10-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132236&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6132236&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Highland Hills Hotels with a Pool ![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/77000000/76460000/76459200/76459163/5496cb17.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) ![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 (3280) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shanae CA $182 CA $213 total includes taxes & fees Nov 23 - Nov 24 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/9cc7a10c.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) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/7012a512.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 (1969) "Very Nice Hotel in a great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $168 CA $197 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/e60db65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/57098577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, soundproofing](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/w3837h2560x3y0-7917acc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed (Specialty)](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/5a3c23ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Chicago/Downtown - The Loop Downtown Chicago 8.8/10 Excellent (1089) "Great stay would recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Reese CA $154 CA $181 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoDowntown-The-Loop.h11062225.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/5dafcd06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/3ff1c0b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/f6491896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/12da6fa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Chicago West Loop Fulton Market Area Downtown Chicago 9.2/10 Wonderful (1004) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) francesca CA $188 CA $220 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-Downtown-West-Loop.h15849775.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/feb0b94d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/7b0fa7fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view from property](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/d1cc0289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/1df0c87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Chicago West Loop Downtown Chicago 8.8/10 Excellent (1060) "Beautiful quite clean property would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Auberney CA $225 CA $264 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/6ad9170a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/a765d2e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/4c94512a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/0f7d6f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area Downtown Chicago 9.2/10 Wonderful (982) "I enjoyed my stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $189 CA $222 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-West-Loop.h15816026.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) ![Standard Double Room, 1 King Bed](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/36d2e00e.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/d06b01bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hoxton Chicago Downtown Chicago 9.0/10 Wonderful (1003) "Great location, very clean, friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $233 CA $273 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/42100/42042/4a671455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/42100/42042/a6b676f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42100/42042/54297010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42042/a0474a5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country inn & Suites by Radisson Bolingbrook, I-55 Bolingbrook 9.2/10 Wonderful (335) "This was a great place to stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valerie CA $132 CA $161 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bolingbrook-Hotels-Country-Inn-Suites-By-Radisson-Bolingbrook.h42042.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/345c3402.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 (298) "Nice hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $136 CA $160 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Suites-Chicago-Medical-District-Uic.h102236658.Hotel-Information) ![Executive lounge](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Suite | Living area](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/54bf755e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Bedroom Suite | Dining room](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/c0679d99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Suite](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/w4238h2832x0y0-ef315dd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Level Chicago Fulton Market Downtown Chicago 9.2/10 Wonderful (336) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yasmine CA $204 CA $271 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Level-Chicago-Fulton-Market.h95823687.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=2025-11-11&endDate=2025-11-12®ionId=6132236&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Highland Hills Hotel Reviews ## Frequently asked questions ### What are some accommodations with pools in Highland Hills? > [SureStay Plus Hotel by Best Western Chicago Lombard](https://www.expedia.ca/Chicago-Hotels-SureStay-Plus-Hotel-By-Best-Western-Chicago-Lombard.h10641.Hotel-Information): Hotel, 3-minute walk from Merchandise Mart. Features a sauna, an indoor pool, and a snack bar/deli. [Crowne Plaza Chicago West Loop by IHG](https://www.expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information): Hotel, 7-minute walk from Allstate Arena. Offers complimentary wireless internet access, an indoor pool, and Smart TVs. [Hyatt Regency O'Hare Chicago](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information): Hotel located near Donald E. Stephens Convention Center. Offers an indoor pool, an outdoor pool, and a snack bar/deli. [voco Chicago Downtown - Riverwalk by IHG](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information): Hotel, 4-minute walk from Donald E. Stephens Convention Center. Provides 3 restaurants, an indoor pool, and complimentary wireless internet access. [Holiday Inn Chicago O'Hare – Rosemont by IHG](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Ohare-Airport.h87702727.Hotel-Information): Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool, and a sauna. ### What is there to see and do in Highland Hills? > Make a point to visit attractions like Morton Arboretum and Addison Ice Arena. During your stay, check out sights such as Yorktown Shopping Center, Oakbrook Center Mall, and Drury Lane Theater. Highland Hills appeals to visitors with its array of dining options and major shopping area. ### When is the best time to book a hotel with a pool in Highland Hills? > You may want to consider an accommodation that has an outdoor pool if you plan to visit in the warmest months of July, August, or June when the average temp is 71°F. 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