Title: Book the Best Hotels with POOL in Downtown Chicago in 2025 | Expedia.ca [Downtown Chicago Travel Guide](https://expedia.ca/Chicago-Downtown-Chicago.dx6350699)[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)[Downtown Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Chicago.d6350699.Car-Rental-Guide)[Downtown Chicago Vacations](https://expedia.ca/Downtown-Chicago.d6350699.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191755-Chicago.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Downtown Chicago, IL from CA $279 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Downtown Chicago Hotels with a Pool Tonight [Sep 24 - Sep 25](https://www.expedia.ca/Hotel-Search?regionId=6350699&startDate=2025-09-24&endDate=2025-09-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=6350699&startDate=2025-09-25&endDate=2025-09-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=6350699&startDate=2025-09-26&endDate=2025-09-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6350699&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Downtown Chicago Hotels with a Pool ## Our top choices for Downtown Chicago hotels with a pool ![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b.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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/00a6df6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8d77a43f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Radisson Blu Aqua Hotel Chicago Downtown Chicago 8.4/10 Very good (1710) "Great location" CA $328 CA $427 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/fcdb86cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/89e1318d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/42397db2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/5785af38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InterContinental Chicago Magnificent Mile by IHG Downtown Chicago 9.0/10 Wonderful (2430) "Great stay " CA $400 CA $514 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2.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/1000000/20000/17300/17288/bebf91fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/c8521e1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/ea1f0698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Swissotel - Chicago Downtown Chicago 9.0/10 Wonderful (2802) "The hotel was in a great location. " CA $290 CA $382 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.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 Downtown Chicago 8.8/10 Excellent (2069) "Staff was very friendly, rooms were cleaned daily, and the onsite restaurant was fantastic!" CA $254 CA $298 total includes taxes & fees Oct 1 - Oct 2 [](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/aaad0ec5.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) ![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 (1985) "Wonderful historic property, we loved our stay in this beautiful hotel" CA $299 CA $385 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/602d4892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.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) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago Downtown Chicago 8.4/10 Very good (2213) "Amazing stay and great location…" CA $274 CA $362 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.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/1000000/580000/570400/570329/71356b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.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) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile Downtown Chicago 8.2/10 Very good (2736) "Great location, good breakfast, and friendly staff!! " CA $281 CA $371 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/57098577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/w3837h2557x3y3-b429e995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Chicago/Downtown - The Loop Downtown Chicago 8.6/10 Excellent (1075) "Great place " CA $303 CA $356 total includes taxes & fees Oct 3 - Oct 4 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoDowntown-The-Loop.h11062225.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/896a6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1faa6c2c.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 (4980) "Really enjoyed our stay!!" CA $258 CA $302 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | View from room](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/3bc31c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/97bbd3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/b1c13209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | Living area](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/4eb87158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Chicago Downtown/Magnificent Mile Downtown Chicago 8.0/10 Very good (1341) "Great hotel and great locations. Close to great restaurants and lot great attractions " CA $238 CA $279 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-DowntownMagnificent-Mile.h10607.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=2025-10-08&endDate=2025-10-09®ionId=6350699&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Price trends for hotels in Downtown Chicago | Less expensive | More expensive | Next month | | --- | --- | --- | | January | June | CA $393 | | Month | Price | | --- | --- | | January | CA $171 | | February | CA $182 | | March | CA $272 | | April | CA $338 | | May | CA $456 | | June | CA $482 | | July | CA $422 | | August | CA $386 | | September | CA $373 | | October | CA $393 | | November | CA $257 | | December | CA $193 | Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Downtown Chicago. Select dates and complete search for nightly totals inclusive of taxes and fees. ## Top Downtown Chicago Hotel Reviews ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Grea5" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Would highly recommend this hotel. Very clean, great happy hour and awesome breakfast! Rooms are very comfortable and quiet" [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "I loved this hotel, I really enjoyed staying there, it was a very convenient area it's close to everything. I would definitely stay there again. Thank you" [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "perfect" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "We really enjoyed staying at the Whitehall during our Chicago visit. From the moment we stepped in, we were warmly welcomed by the staff. The room was large,clean,and the air conditioning worked great. The breakfast area was lovely and had plenty of great varieties to choose from. The location was top notch and on a quieter street. My only complaint is that the wifi connection is poor. We will likely stay again." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Hilton Chicago](//images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "I thoroughly enjoyed my stay at the Chicago Hilton. Loved the ambiance and the inspiring architecture on entering and the old fashioned elevator lobby was a treat itself. The Irish Pub was outstanding with a nice atmosphere and not overly sports oriented like some. I was there during some kind of trade event but the place never felt crowded or had long waits for anything. My room on the 18th floor was a little spartan for my liking, though quite large, however for the amount spent I expected more. Had a nice view and was quiet enough so I’m not taking points away, but yes - a room update is past due if other rooms were like mine. " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "The hotel was clean, staff was friendly and helpful and great location to get to everything. I would definitely stay there again. This my 7th time ive been to" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "It was a great hotel!! The room was awesome and the view from our floor was beautiful. We were so close to Navy Pier which was definitely a plus. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Great location, close to different restaurants and coffee shops. Sadly the pool was closed when I was there but it looked like the property was very well maintained. Staff was so nice upon check in. Our room was nice and comfortable! Enjoyed my stay and will be back!!" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ## Frequently asked questions ### What's it like visiting Downtown Chicago? > If relaxing by the pool is your idea of a great vacation, you might want to think about lively Downtown Chicago, which offers 64 places to stay with pools. While you're here, you can explore sights such as Michigan Avenue and Navy Pier, and then unwind poolside at one of the accommodations in Downtown Chicago that guests like for their pools. ### What are some hotels with pools in Downtown Chicago? > [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. Features full, an indoor pool, and flat-screen televisions. [Holiday Inn & Suites Chicago - Downtown by IHG](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Suites-Chicago-Downtown.h201274.Hotel-Information): Hotel, 10-minute walk from Willis Tower. Offers a snack bar/deli, a seasonal outdoor pool, and complimentary wireless internet access. [Hilton Garden Inn Chicago Downtown South Loop](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information): Hotel, 1-minute walk from State Street. Provides a snack bar/deli, a pool, and complimentary wireless internet access. [Hyatt Centric Chicago Magnificent Mile](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information): Hotel, 2-minute walk from Michigan Avenue. Features complimentary wireless internet access, an indoor pool, and a 24-hour fitness center. [Homewood Suites by Hilton Chicago Downtown South Loop](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-South-Loop.h33387384.Hotel-Information): Hotel, 2-minute walk from State Street. Offers a snack bar/deli, a pool, and buffet. ### How many hotels with pools are there in Downtown Chicago? > Expedia's 64 hotels in Downtown Chicago give you a great choice for your poolside getaway. ### What is there to see and do in Downtown Chicago? > Explore places like Michigan Avenue, Navy Pier, and Lake Michigan while you're in Downtown Chicago. Make a point to visit attractions like Millennium Park and Dave & Buster's. Downtown Chicago appeals to visitors with its beautiful river views, stunning architecture, and top museums. ### When is the best time to book a hotel with a pool in Downtown Chicago? > You may want to consider a place to stay that offers an outdoor if you'll be visiting in the hottest months of July, August, or June when the average temp is 70°F. 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