Title: Book the Best Hotels with POOL in Near West Side in 2026 | Expedia.ca [Near West Side Travel Guide](https://expedia.ca/Chicago-Near-West-Side.dx6132434)[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 West Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-West-Side.d6132434.Car-Rental-Guide)[Near West Side Vacations](https://expedia.ca/Near-West-Side.d6132434.Destination-Travel-Guides) ![Chicago_UnitedCenter_6064077_01](https://images.trvl-media.com/place/6064077/45e0cfe3-9e5f-4653-8161-042a957b09fc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6064077/45e0cfe3-9e5f-4653-8161-042a957b09fc.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 Near West Side Hotels with a Pool Tonight [Apr 3 - Apr 4](https://www.expedia.ca/Hotel-Search?regionId=6132434&startDate=2026-04-03&endDate=2026-04-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 4 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6132434&startDate=2026-04-04&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6132434&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=6132434&startDate=2026-04-10&endDate=2026-04-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Near West Side hotels with a pool ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/35000000/34770000/34761400/34761378/9752c1a4.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/f598823d.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 (1,005 reviews) - Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat. CA $212 CA $290 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/6b730d6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/19637b91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive lounge](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Level Chicago Fulton Market [](https://www.expedia.ca/Chicago-Hotels-Level-Chicago-Fulton-Market.h95823687.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (437 reviews) - Dive into Chicago's vibrant atmosphere with a seasonal outdoor pool perched in an upscale urban setting. CA $226 CA $300 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Level-Chicago-Fulton-Market.h95823687.Hotel-Information) ![Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/9b3b5e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/84bc7418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/a1547b1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/ef156c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Chicago - Downtown by IHG [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Suites-Chicago-Downtown.h201274.Hotel-Information) Downtown Chicago 8.6/10 Excellent (1,006 reviews) - A refreshing seasonal escape awaits at this Chicago hotel's sun-drenched pool area. CA $153 CA $196 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Suites-Chicago-Downtown.h201274.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) ![Lobby](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/fa1d7c48.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) ![Bar (on property)](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/db5b7e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt House Chicago West Loop [](https://www.expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,210 reviews) - Splashy indoor pool luxury awaits with designer touches in Chicago's West Loop scene. CA $222 CA $260 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information) ![Indoor pool, open 6:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/486e1134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Designer toiletries, hair dryer, bathrobes, towels](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/ccd16d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/fbfdc974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Sake) | Living area](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/ed0b16bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobu Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (812 reviews) - Sleek indoor pool retreat with sun loungers and steam room offers luxe downtown sanctuary. CA $341 CA $400 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.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) ![Lobby](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/8c126093.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) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15850000/15849800/15849775/10a353c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Chicago West Loop Fulton Market Area [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-Downtown-West-Loop.h15849775.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,006 reviews) - Splash into urban relaxation at this West Loop hotel's stylish indoor pool, where sun loungers invite post-sightseeing unwinding. CA $248 CA $291 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Chicago-Downtown-West-Loop.h15849775.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) ![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/0f7d6f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/4dbc75df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15820000/15816100/15816026/aa5910b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area [](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-West-Loop.h15816026.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,000 reviews) - Swim year-round at the urban indoor pool oasis with sun loungers and downtown Chicago views. CA $266 CA $313 total includes taxes & fees Apr 10 - Apr 11 [](https://www.expedia.ca/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-West-Loop.h15816026.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/4f2b2c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/74cfecc9.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) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102236700/102236658/0d35e1b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Chicago Medical District UIC [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Suites-Chicago-Medical-District-Uic.h102236658.Hotel-Information) Near West Side 9.6/10 Exceptional (534 reviews) - Sleek indoor pool oasis at Chicago medical district hotel offers year-round swimming bliss. CA $212 CA $249 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Suites-Chicago-Medical-District-Uic.h102236658.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.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 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) Downtown Chicago 8.6/10 Excellent (3,157 reviews) - Splash into the city at this downtown hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match. CA $134 CA $157 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17.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) ### Hilton Chicago/Magnificent Mile Suites [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (4,044 reviews) CA $180 CA $211 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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=2026-04-18&endDate=2026-04-19®ionId=6132434&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Near West Side Breakfast included 4 stars 5 stars Hot tub Spa ## Top Near West Side Hotel Reviews ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 2/10 Terrible "NO AC in the spring time. Both our rooms were over 75 degrees and humid beginning of April. I asked if the AC was working and said that it is a “green efficient building” and that they don’t turn the AC on until summer which I thought was an April fools joke at first because it was uncomfortable temperature wise, especially for sleeping. If you take showers then the humidity rises even more. They did offer to bring up a box fan which made it feel like I was back in summer camp but for $200+ a night. Also, we put on the reservation that was had 4 children and they didn’t give us connecting rooms, in fact they weren’t even on the same floor. I’d give it a 2 /5 stars. I would give it a 1 star but I didn’t see any bedbugs like some other online reviews said so that was nice at least." [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![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 "I think you took advantage of people needing a place to stay when their flight was cancelled. The price was very inflated but we had very little choice about where we could stay. " [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.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 experience " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Holiday Inn & Suites Chicago - Downtown by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/9b3b5e62_y.jpg) ### Holiday Inn & Suites Chicago - Downtown by IHG 10/10 Excellent " ." [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Suites-Chicago-Downtown.h201274.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 8/10 Good "The hotel is very nice overall! We loved the games area in the lobby! Maybe it’s just that they’re extremely short staffed for the size of the place, but when disappointments keep happening you start to feel let down. Expect long lines at the front desk for check in or anything else. We couldn't get a response about getting an extra blanket for the room and they only have an automated system to help you with guest service. We also had to wait a couple hours for our luggage to get to the room after we arrived which was inconvenient. Also, heads up - we weren’t made aware at check in that the pool/hot tub area closes at 9:45 pm and that you need a reservation after 2:30 pm so we weren’t able to use either when we were there. That was a bummer for the kids since that’s why we booked this hotel!" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/871940a9_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 4/10 Poor "The room was clean. The staff was very friendly. However, I specifically chose this hotel because parking was available. When we arrived, however, parking was not available. I was instructed that there was a lot down the street, outside, and I could park there. It was very inconvenient, especially since I had a friend with me who is not capable of walking the few blocks and uses a cane. After asking several times, I was told that some Parking had opened the following morning and I moved the car. I was then charged $87 overnight instead of the advertised 54\. The other issue is the fact that there was absolutely no water available in my room the second morning of my visit. There was apparently a plumbing issue and the entire hotel was out. I understand that these things happen, but there was no attempt made to make accommodations or provide water when I inquired at the front desk. There was no running water in the entire hotel, no restrooms, no faucets, nothing. Again, I understand that things happen, however, my bill totaled over $450 for two nights accommodations. Not outrageous, but not an insignificant amount, considering two of the major amenities that I had hoped to expect were unavailable. " [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h2559x0y3-c577bf94_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "This hotel is great! Great location, great staff. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Stayed here several times. This is the only place I stay in Chicago and always a five star experience!" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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 "It is in a good location not far from public transit and the magnificent. The coffee in the morning is very good." [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ## Frequently asked questions ### What's it like visiting Near West Side? ### What are some accommodations with pools in Near West Side? ### How many hotels with pools are there in Near West Side? ### What is there to see and do in Near West Side? ### When is the best time to book a hotel with a pool in Near West Side? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [All Inclusive Resorts and in Chicago ](https://www.expedia.ca/Chicago-Hotels-All-Inclusive-Hotel.0-0-d178248-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Business-Hotel.0-0-d178248-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Cheap-Hotels.0-0-d178248-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Chicago ](https://www.expedia.ca/Chicago-Hotels-Couples-Resorts-Hotels.0-0-d178248-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - 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