Title: Book the Best Hotels with POOL in Near East Side 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)[Near East Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-East-Side.d553248633938968461.Car-Rental-Guide)[Near East Side Vacations](https://expedia.ca/Near-East-Side.d553248633938968461.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/579e42b9259c74616d62fad104490806.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Deano # Find Hotels with a Pool in Near East Side, IL from CA $166 ![](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 East Side Hotels with a Pool Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=553248633938968461&startDate=2025-10-20&endDate=2025-10-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=553248633938968461&startDate=2025-10-21&endDate=2025-10-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248633938968461&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248633938968461&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Near East Side 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) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8de272e8.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/f5341c22.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 Downtown Chicago 8.6/10 Excellent (1750) "Excellent Location and beautiful views from the rooms!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $270 CA $360 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/w4000h2645x0y22-fdcb2993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/0d225744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/bd0f84f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/5bfebb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The St. Regis Chicago Downtown Chicago 9.2/10 Wonderful (77) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $777 CA $912 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/c042bdff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade Downtown Chicago 8.4/10 Very good (1385) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam CA $189 CA $222 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![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/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) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG Downtown Chicago 8.8/10 Excellent (3237) "Great location and fantastic staff who were always happy to help. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Victoria CA $247 CA $290 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/5e299c2d.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/b9be2277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile Downtown Chicago 8.4/10 Very good (4111) "Clean room , staff were friendly, a lot of restaurants in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen CA $168 CA $197 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/520a670b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 2 Double Beds, Non Smoking, Refrigerator (with Sofabed)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/aeb6fede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/b6152ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f7f78ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western River North Hotel Downtown Chicago 7.8/10 Good (1031) "Great stay" ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Bart CA $142 CA $166 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/6dc8c836.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/34000000/33690000/33682500/33682469/fe59f9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown South Loop Downtown Chicago 8.8/10 Excellent (1702) "Excellent hotel in a wonderful location of Chicago!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $148 CA $173 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.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) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.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) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2873) "Had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josh CA $177 CA $207 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/698b65d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/f6a223b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/baa44a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/ddbc274d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loews Chicago Hotel Downtown Chicago 9.4/10 Exceptional (1571) "Great stay, comfy beds!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brea CA $321 CA $421 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Chicago-Hotels-Loews-Chicago-Hotel.h9059537.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) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.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 (5129) "Great place, good breakfast and the location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) NATIA CA $201 CA $236 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.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=2025-11-03&endDate=2025-11-04®ionId=553248633938968461&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Near East Side Hotel Reviews ![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 "Parking was terrible and expensive. Recommend valet parking. Staff, very hard to talk to and i arrived at 3:30 scheduled to check in at 4 pm. Room wasn't available until 4;30. Staff wasn't to concerned." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.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 "Nice location, rooms were nice size beds were comfortable water pressure was great " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "The room was great, view gorgeous and all the hotel staff were welcoming and helpful! Location of the hotel is perfect to walk or take the metro. The restaurant had limited choices for breakfast but was nice enough and convenient." [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "It was affordable " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Crowne Plaza Chicago West Loop by IHG](//images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "Excellent staff and overall experience. " [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "I like it" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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 "Clean room, little cold but we fixed that! Staff was very accommodating and helpful!" [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Swissotel - Chicago](//images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg) ### Swissotel - Chicago 10/10 Excellent "Nice property conveniently located." [](https://expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "The area was amazing " [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Near East Side? > [Swissotel - Chicago](https://www.expedia.ca/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information): Hotel, 5-minute walk from Michigan Avenue. Offers a seasonal outdoor pool, an indoor pool, and a 24-hour fitness center. [Radisson Blu Aqua Hotel Chicago](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information): Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool, and flat-screen televisions. [Congress Plaza Hotel](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information): Hotel, 4-minute walk from Michigan Avenue. Offers complimentary wired internet access, an indoor pool, and LCD televisions. [Freehand Chicago](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information): Hotel, 3-minute walk from Michigan Avenue. Features a snack bar/deli, an indoor pool, and complimentary wireless internet access. [Hilton Chicago/Magnificent Mile Suites](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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 Near East Side? > While you're in the area, consider exploring places like Michigan Avenue, Navy Pier, and Wrigley Field. Make a point to visit attractions like Ohio Street Beach and Chicago Children's Museum. Near East Side appeals to visitors with its beautiful river views and array of dining options. ### When is the best time to book a hotel with a pool in Near East Side? > You may want to consider an accommodation with an outdoor swimming pool if you'll be visiting in the warmest months of July, August, or June when the average temp is 70°F. 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