Title: Book the Best Hotels with POOL in Streeterville in 2026 | Expedia.ca [Streeterville Travel Guide](https://expedia.ca/Chicago-Streeterville.dx6130109)[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)[Streeterville Car Rentals](https://expedia.ca/Car-Rentals-In-Streeterville.d6130109.Car-Rental-Guide)[Streeterville Vacations](https://expedia.ca/Streeterville.d6130109.Destination-Travel-Guides) ![Navy Pier which includes wild flowers and general coastal views as well as a couple](https://images.trvl-media.com/place/6069215/5854ad1a-e5a8-41d6-a235-77f0217d4701.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Streeterville, IL from CA $131 - ![](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 Streeterville Hotels with a Pool Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2025-12-12&endDate=2025-12-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2025-12-13&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6130109&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Streeterville hotels with a pool ![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) ![Banquet hall](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/2ad62276.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 (2953) "Great location, the staff was friendly and the room was very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Breanna CA $112 CA $131 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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) ![Reception](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/0ea4e737.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) ![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/ec33d4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) Downtown Chicago 8.2/10 Very good (2741) "Great food clean room friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARINA CA $110 CA $170 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.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) ![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) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/b90174ec.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) ### 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 (1048) "Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hannah CA $135 CA $199 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.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/1000000/30000/21200/21152/8e39b688.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 (2183) "Nice Hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan CA $123 CA $144 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/da99f4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6ec865cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) Downtown Chicago 8.4/10 Very good (1513) "Everything was really wonderful.. would stay again for sure!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexa CA $139 CA $163 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.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) ![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) ![View from property](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/3d8cc8f8.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 (1594) "Great location and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric Lynn CA $135 CA $158 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/311c65a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, Netflix, pay movies, streaming services](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/cccba568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4a14c915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4c0ebbe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Grand Chicago Riverwalk [](https://www.expedia.ca/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.Hotel-Information) Downtown Chicago 8.4/10 Very good (1579) "Rooms were very nice and staff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $205 CA $282 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Chicago-Hotels-Sheraton-Grand-Chicago.h12167.Hotel-Information) ![Seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/949e3d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/0347f2d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/bc751856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Grand Vacations Club Chicago Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hilton-Grand-Vacations-Chicago-Downtown-Magnificent-Mile.h37641670.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (325) "Great accommodation, staff really nice, room was spacious and very clean. Perfect location to walk just about anywhere, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lizbeth CA $206 CA $242 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Grand-Vacations-Chicago-Downtown-Magnificent-Mile.h37641670.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/acbf2aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/5616df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/bbac06a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (1004) "Excellent service throughout the hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $625 CA $734 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/f0e0ee26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Terrace (Lakeshore) | Lake view](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/e5b56b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/ee956af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/1e19db6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (999) "Amazing hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $579 CA $679 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.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=2025-12-27&endDate=2025-12-28®ionId=6130109&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Streeterville Hotel Reviews ![Embassy Suites by Hilton Chicago Downtown Magnificent Mile](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e_y.jpg) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile 10/10 Excellent "Clean room and friendly staff, overall good stay " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Great place always. " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "great hotel in a great city" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg) ### The Peninsula Chicago 10/10 Excellent "My favorite! " [](https://expedia.ca/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Great room with double bathroom. Executive level with private elevator." [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Wonderful room, great location and friendly helpful staff. The breakfast buffet is really well done." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "The room was beautiful. I booked the Premium lake view room. It came with a King bed and a wonderful view. I just wish the room had a microwave but there was a microwave in the grab and go area. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.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 "Loved it" [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Hyatt Centric Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53_y.jpg) ### Hyatt Centric Chicago Magnificent Mile 10/10 Excellent "Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food." [](https://expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.Hotel-Information) ## Frequently asked questions ### What's it like visiting Streeterville? ### What are some hotels with pools in Streeterville? ### How many pool hotels will I find in Streeterville? ### What is there to see and do in Streeterville? ### When is the best time to book a hotel with a pool in Streeterville? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [3 Star Hotels in Magnificent Mile ](https://www.expedia.ca/3Star-Magnificent-Mile-Chicago-Hotels.s30-n800025-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Magnificent Mile ](https://www.expedia.ca/4Star-Magnificent-Mile-Chicago-Hotels.s40-n800025-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Magnificent Mile ](https://www.expedia.ca/5Star-Magnificent-Mile-Chicago-Hotels.s50-n800025-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Chicago ](https://www.expedia.ca/Chicago-Hotels-Business-Hotel.0-0-d178248-tBusinessHotel.Travel-Guide-Filter-Hotels) - 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