Title: Book the Best Hotels with POOL in Chicago in 2026 | Expedia.ca [Chicago Travel Guide](https://expedia.ca/Chicago.dx178248)[Hotels in Chicago](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[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)[Chicago Car Rentals](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[Chicago Vacation Packages](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides) ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.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 Chicago Hotels with a Pool Tonight [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-13&endDate=2026-01-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=178248&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chicago 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) ![Banquet hall](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/2ad62276.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) ![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 (3,044 reviews) "All around a nice stay for the holiday " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alec CA $106 CA $124 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.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) ![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 (2,238 reviews) "Great hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $118 CA $139 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/f57ccf79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/e1eb307d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Royal Sonesta Chicago River North [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (2,391 reviews) "Lovely staff, very clean hotel, convenient location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tierra CA $137 CA $206 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.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) ![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) ### 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 (1,068 reviews) "Amazing location, excellent service and great pool and hot tub. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $136 CA $200 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-Chicago-Magnificent-Mile.h151139.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) ![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/1000000/10000/1400/1346/6ec865cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.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 (1,597 reviews) "Easy check in and out, excellent room service and dining menu." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin Bradford CA $140 CA $165 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.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) ![Sports facility](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/5bee96cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/e065e04c.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) ### Hilton Garden Inn Chicago Downtown South Loop [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) Downtown Chicago 8.8/10 Excellent (1,812 reviews) "Staff was great hotel clean close to a lot of dining and stores " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $105 CA $123 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.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) ![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) ![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 (2,791 reviews) "Great hotel staff and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline CA $132 CA $196 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/f36e2ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/dec7b24e.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d288265e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) Downtown Chicago 8.6/10 Excellent (4,318 reviews) "Amazing staff and perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandi CA $108 CA $127 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.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) ![In-room safe, desk, laptop workspace, free cribs/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/085d232b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/e9e7f382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/f1a5921f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) Downtown Chicago 8.8/10 Excellent (3,593 reviews) "Great location and breakfast.. can be a bit pricey but worth it. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Shaurya CA $173 CA $204 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) ![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/fd4d7555.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/w2880h1919x0y0-235561ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/df6e8a36.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/5000000/4530000/4520700/4520626/44865590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Radisson Blu Aqua Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information) Downtown Chicago 8.6/10 Excellent (1,823 reviews) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yavuz CA $195 CA $265 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.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=2026-01-27&endDate=2026-01-28®ionId=178248&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Chicago Hotel Reviews ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Great location. Hotel was clean and comfortable. Staff were very friendly and welcoming. Only problem is that I paid for parking ($92) with my reservation thru Hotels.com and now I see on my credit card that the hotel also charged me for parking. Now I have to fix that problem. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](https://images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Girls trip / business meeting " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.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 staff, nice pool and big room! " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Great staff, great location." [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "Amazing" [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg) ### Silversmith Hotel Chicago Downtown 10/10 Excellent "Fantastic location for the el. Rooms Are somewhat dated with paint and carpet, but we weren’t there to spend time in the room. So I don’t fault them for any of that. Some of the carpet is coming up from floors which is a trip hazard and should be addressed but again- not something that’s affecting their rating. The bed was very comfortable, good WiFi; excellent bathroom water pressure and very hot water which is nice. Close to the CSO, all access for the CTA and great restaurants near by. I do not recommend eating at the restaurant on site- you can be anywhere in the city in 20 minutes from the el platform so I highly Recommend staying here if you’re open to walking and exploring " [](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg) ### Club Quarters Hotel Wacker at Michigan, Chicago 10/10 Excellent "Super fast and easy check in / out experience, amazing location and very affordable " [](https://expedia.ca/Chicago-Hotels-Club-Quarters-Hotel.h889753.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 "Great hotel " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Holiday Inn Chicago Dwtn - The Mart by IHG](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg) ### Holiday Inn Chicago Dwtn - The Mart by IHG 10/10 Excellent "I love staying here. Great View. Staff is friendly. " [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Chicago with outdoor pools? > Another excellent option is the [Viceroy Chicago](https://www.expedia.ca/Chicago-Hotels-Viceroy-Chicago.h18614145.Hotel-Information), also rated 9.4, offering a chic outdoor pool experience with sun loungers for relaxing afternoons. Guests rave about the beautiful and clean rooms, and the staff's excellent service makes every stay feel special. Conveniently located in a vibrant shopping district, this 4.5-star hotel combines comfort with style, making it superb for those who want both adventure and relaxation. > > > For those in search of an upscale experience, [Nobu Hotel Chicago](https://www.expedia.ca/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) stands out with its luxurious outdoor pool and impeccable service. With a superb rating of 9.4, this 5-star hotel provides guests with premium amenities, including deep soaking bathtubs and designer toiletries. The friendly staff and fantastic room quality ensure a memorable stay, making it ideal for families looking to indulge during their trip. > > > [Kasa River North Chicago](https://www.expedia.ca/Chicago-Hotels-Kasa-River-North-Chicago.h66425311.Hotel-Information), rated 9.6, offers a more casual yet equally appealing option with its rooftop terrace and outdoor pool. Families will appreciate the well-equipped kitchen facilities and free Wi-Fi, superb for those who enjoy a cozy feel while traveling. The friendly front desk staff and fantastic amenities further enhance the overall experience. > > > Lastly, the [Hampton Inn & Suites Chicago Downtown](https://www.expedia.ca/Chicago-Hotels-Hampton-Inn-Suites-Chicago-Downtown.h79589.Hotel-Information), with a rating of 9.2, provides a budget-friendly option featuring a warm outdoor pool and complimentary breakfast. Families will love the spacious rooms and the welcoming atmosphere, making it a great choice for a fun-filled Chicago getaway. > > > Each of these hotels not only offers outdoor pools but also a range of amenities that cater to families and adventurous travellers alike. ### How much does a hotel with outdoor pool in Chicago cost? ### What are some of the best Chicago hotels with outdoor pools and scenic views? > Another great choice is the [Viceroy Chicago](https://www.expedia.ca/Chicago-Hotels-Viceroy-Chicago.h18614145.Hotel-Information), also rated at 4.5 stars and boasting a beautiful outdoor pool area. Guests enjoy lounging on the sun loungers while soaking in picturesque lake views. With a traveller score of 9.4, it's no surprise that many reviews highlight the hotel's great location and the excellent quality of service provided by the friendly staff. > > > For those who prefer a central location, the [Renaissance Chicago Downtown Hotel](https://www.expedia.ca/Chicago-Hotels-Renaissance-Chicago-Downtown-Hotel.h19215.Hotel-Information) offers an inviting outdoor pool with lovely river views. This 4-star hotel holds a solid traveller rating of 9.2, with many guests praising the helpful staff and the quality of food and drinks available on-site. > > > Finally, [The Ritz-Carlton, Chicago](https://www.expedia.ca/Chicago-Hotels-The-Ritz-Carlton.h14447.Hotel-Information) stands out as a luxurious 5-star option, featuring an outdoor pool with captivating lake views that guests find exceptional. With a traveller rating of 9.2, this hotel is known for its beautiful rooms and outstanding service, making it a worthy choice for a memorable stay. ### Are there hotels in Chicago with outdoor pool cabanas or loungers? > For those looking for a family-friendly option, the [Holiday Inn Express & Suites Chicago Schaumburg by IHG](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Suites-Chicago-Schaumburg.h102855105.Hotel-Information) also shines with its outdoor pool that includes free cabanas and sun loungers. Rated 9.0 by travellers, this hotel offers a spacious and convenient stay, complemented by a complimentary buffet breakfast that is both delicious and satisfying. > > > The [Radisson Blu Aqua Hotel Chicago](https://www.expedia.ca/Chicago-Hotels-Radisson-Blu-Aqua-Hotel-Chicago.h4520626.Hotel-Information) offers a touch of luxury with its resort-style outdoor pool, complete with free cabanas and sun loungers. Guests appreciate the beautiful and clean rooms, along with exceptional service, earning the hotel a great rating of 8.6. > > > Lastly, families can enjoy a fun-filled stay at the [Great Wolf Lodge Illinois](https://www.expedia.ca/Chicago-Hotels-Great-Wolf-Lodge-Illinois.h1871214.Hotel-Information), which features both indoor and outdoor pools, along with cabanas. With a rating of 8.6, this hotel is well-loved for its clean rooms and amazing water park, ensuring that everyone in the family has a blast. ### Which Chicago hotels with outdoor pools are near Chicago, IL (MDW-Midway Intl.)? > In addition to the inviting pool area, you'll find plenty of amenities designed to enhance your stay. Guests rave about the clean and spacious rooms, equipped with essentials such as free Wi-Fi and complimentary toiletries. Families traveling with young children will appreciate the availability of cribs at no extra charge, ensuring a straightforward experience. > > > Moreover, the hotel provides a 24-hour airport shuttle service, making it incredibly convenient for those arriving or departing from the airport. Self-parking is also free, adding to the overall value of your stay. ### Which Chicago hotels offer poolside service for food and drinks? > Another great option is [The Robey, Chicago, a Member of Design Hotels](https://www.expedia.ca/Chicago-Hotels-The-Robey.h15758132.Hotel-Information). With a traveller review score of 9.2, this 3.5-star hotel also features a poolside bar that enhances the overall experience for guests looking to relax by the water. Visitors love the beautiful, clean rooms and the attentive staff, ensuring that your time spent poolside is both enjoyable and convenient. > > > [Hilton Grand Vacations Club Chicago Magnificent Mile](https://www.expedia.ca/Chicago-Hotels-Hilton-Grand-Vacations-Chicago-Downtown-Magnificent-Mile.h37641670.Hotel-Information) is yet another hotel to consider, offering a poolside bar alongside spacious rooms and convenient amenities. Guests appreciate the great location and friendly service here, contributing to its rating of 9.2. > > > For a stylish, urban vibe, [The Hoxton Chicago](https://www.expedia.ca/Chicago-Hotels-The-Hoxton-Chicago.h34761378.Hotel-Information) stands out with its poolside bar and a score of 9.0\. This 4-star hotel not only provides a lively option but also features friendly staff and comfortable, super clean rooms, making it a delightful option for families wanting to unwind. > > > Lastly, [The Hotel at Midtown](https://www.expedia.ca/Chicago-Hotels-The-Hotel-At-Midtown.h18385274.Hotel-Information) combines leisure with fitness, offering a poolside bar as well. This 4-star property, rated 9.0, is known for its beautiful rooms and fantastic amenities, ensuring that both relaxation and fun are on the agenda for your stay. ### Is it cheaper to book flights and a hotel in Chicago as a package? ### How can I save on a hotel in Chicago with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [2 Star Hotels in The Loop ](https://www.expedia.ca/2Star-The-Loop-Chicago-Hotels.s20-n800024-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in The Loop ](https://www.expedia.ca/3Star-The-Loop-Chicago-Hotels.s30-n800024-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Loop ](https://www.expedia.ca/4Star-The-Loop-Chicago-Hotels.s40-n800024-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Loop ](https://www.expedia.ca/5Star-The-Loop-Chicago-Hotels.s50-n800024-0.Travel-Guide-Filter-Hotels) - [Hotels near Adams-Wabash Station ](https://www.expedia.ca/Adams-Wabash-Station-Hotels.d6210258.Travel-Guide-Hotels) - [Houseboats in Adams-Wabash Station ](https://www.expedia.ca/Adams-Wabash-Station-Houseboats.d6210258-aaHouseboats.Travel-Guide-Accommodation) - [Hotels near Art Institute of Chicago ](https://www.expedia.ca/Art-Institute-Of-Chicago-Hotels.0-l6064021-0.Travel-Guide-Filter-Hotels) - [Hotels near CIBC Theatre ](https://www.expedia.ca/CIBC-Theatre-Hotels.0-l553248621563220853-0.Travel-Guide-Filter-Hotels) - [Hotels near Chagall's Four Seasons ](https://www.expedia.ca/Chagalls-Four-Seasons-Hotels.0-l553248621533116569-0.Travel-Guide-Filter-Hotels) - [Hotels near Chase Tower ](https://www.expedia.ca/Chase-Tower-Hotels.0-l553248621555594882-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Temple ](https://www.expedia.ca/Chicago-Temple-Hotels.0-l553248621561883126-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Theatre ](https://www.expedia.ca/Chicago-Theatre-Hotels.0-l6064049-0.Travel-Guide-Filter-Hotels) - [Hotels near Cloud Gate ](https://www.expedia.ca/Cloud-Gate-Hotels.0-l6182888-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Business-Hotel.0-n6350699-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Couples-Resorts-Hotels.0-n6350699-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Golf-Hotel.0-n6350699-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Green Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Green-Sustainable.0-n6350699-0-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-A-Lazy-River.0-n6350699-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Childcare.0-n6350699-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Tennis-Courts.0-n6350699-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Hotels-With-Waterslides.0-n6350699-0-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Mountain-Hotels.0-n6350699-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Ski Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Ski-Hotel.0-n6350699-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Waterpark-Hotels.0-n6350699-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Downtown Chicago ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels-Winery-Hotel.0-n6350699-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Downtown Chicago Hotels ](https://www.expedia.ca/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Madison-Wabash Station ](https://www.expedia.ca/Madison-Wabash-Station-Apart-Hotels.d6210251-aaApartHotels.Travel-Guide-Accommodation) - [Hotels near Madison-Wabash Station ](https://www.expedia.ca/Madison-Wabash-Station-Hotels.d6210251.Travel-Guide-Hotels) - [Inns in Madison-Wabash Station ](https://www.expedia.ca/Madison-Wabash-Station-Inns.d6210251-aaInns.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Romantic-Hotel.0-n800025-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Waterpark-Hotels.0-n800025-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Magnificent Mile ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Winery-Hotel.0-n800025-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Magnificent Mile Hotels ](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels) - [Hotels near Millennium Park ](https://www.expedia.ca/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels) - [Hotels near Monroe Station ](https://www.expedia.ca/Monroe-Station-Hotels.d6189309.Travel-Guide-Hotels) - [Houseboats in Monroe Station ](https://www.expedia.ca/Monroe-Station-Houseboats.d6210064-aaHouseboats.Travel-Guide-Accommodation) - [Hotels near Richard J. Daley Center ](https://www.expedia.ca/Richard-J-Daley-Center-Hotels.0-l6175173-0.Travel-Guide-Filter-Hotels) - [River North Hotels ](https://www.expedia.ca/River-North-Chicago-Hotels.0-n6350695-0.Travel-Guide-Filter-Hotels) - [Hotels near State Street ](https://www.expedia.ca/State-Street-Hotels.0-l6175182-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Adults-Only-Resorts.0-n800024-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-All-Inclusive-Hotel.0-n800024-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Beach-Hotel.0-n800024-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Best-Western.0-n800024-0--bBestWestern.Travel-Guide-Filter-Hotels) - [Boutique Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Boutique-Hotel.0-n800024-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Cheap-Hotels.0-n800024-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Club Quarters Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Club-Quarters.0-n800024-0--bClubQuarters.Travel-Guide-Filter-Hotels) - [Destination Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Destination-Hotels.0-n800024-0--bDestinationHotels.Travel-Guide-Filter-Hotels) - [Fairmont Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Fairmont.0-n800024-0--bFairmont.Travel-Guide-Filter-Hotels) - [Family Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Family-Hotel.0-n800024-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Golf-Hotel.0-n800024-0-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hilton Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hilton-Hotels.0-n800024-0--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Honeymoon-Hotels.0-n800024-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Early-Check-In.0-n800024-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Pool.0-n800024-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Balconies.0-n800024-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Bar in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Bar.0-n800024-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Airport-Shuttle.0-n800024-0-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Breakfast.0-n800024-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Free-Parking.0-n800024-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Hot-Tubs.0-n800024-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n800024-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Kitchenettes.0-n800024-0-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotels-With-Tennis-Courts.0-n800024-0-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Kimpton Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Kimpton-Hotels.0-n800024-0--bKimptonHotels.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-LGBT-Friendly-Hotel.0-n800024-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Lake Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Lake-Hotels.0-n800024-0-tLakeHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Luxury-Hotel.0-n800024-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Marriott-Hotels-Resorts.0-n800024-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Oceanfront-Hotels.0-n800024-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Pet-Friendly-Hotel.0-n800024-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Romantic-Hotel.0-n800024-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Shopping Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Shopping-Hotel.0-n800024-0-tShoppingHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Ski-Hotel.0-n800024-0-tSkiHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Spa-Hotel.0-n800024-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in The Loop ](https://www.expedia.ca/The-Loop-Chicago-Hotels-Waterpark-Hotels.0-n800024-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [The Loop Hotels ](https://www.expedia.ca/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Theatre District ](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Cheap-Hotels.0-n651190586167894016-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Theatre District ](https://www.expedia.ca/Theatre-District-Chicago-Hotels-Luxury-Hotel.0-n651190586167894016-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Theatre District Hotels ](https://www.expedia.ca/Theatre-District-Chicago-Hotels.0-n651190586167894016-0.Travel-Guide-Filter-Hotels) - [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Cibc Theatre ](https://www.expedia.ca/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction) - [Visit Downtown Chicago ](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699) - [Visit The Loop ](https://www.expedia.ca/Chicago-The-Loop.dx800024) - [Millennium Park ](https://www.expedia.ca/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) - [Richard J. Daley Center ](https://www.expedia.ca/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [The Loop Vacations ](https://www.expedia.ca/The-Loop.d800024.Destination-Travel-Guides) - [Alamo Rent A Car Rental Cars in The Loop ](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c6.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in The Loop ](https://www.expedia.ca/Avis-Car-Rentals-In-The-Loop.d800024-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Richard J. Daley Center ](https://www.expedia.ca/Car-Rentals-In-Richard-J-Daley-Center.d6175173.Car-Rental-Guide) - [Car rentals near The Loop ](https://www.expedia.ca/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide) - [Dollar Rent A Car Rental Cars in The Loop ](https://www.expedia.ca/Dollar-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c43.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in The Loop ](https://www.expedia.ca/Enterprise-Car-Rentals-In-The-Loop.d800024-c15.Car-Rental-Guide-Suppliers) - [Fox Rental Cars Rental Cars in The Loop ](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-The-Loop.d800024-c19.Car-Rental-Guide-Suppliers) - [Oryx Rent A Car Rental Cars in The Loop ](https://www.expedia.ca/ORYX-Rent-A-Car-Car-Rentals-In-The-Loop.d800024-c1059.Car-Rental-Guide-Suppliers) - [Payless Rental Cars in The Loop ](https://www.expedia.ca/Payless-Car-Rentals-In-The-Loop.d800024-c38.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in The Loop ](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-The-Loop.d800024-c33.Car-Rental-Guide-Suppliers) - [Routes Rental Cars in The Loop ](https://www.expedia.ca/Routes-Car-Rentals-In-The-Loop.d800024-c1101.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in The Loop ](https://www.expedia.ca/Sixt-Car-Rentals-In-The-Loop.d800024-c35.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in The Loop ](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-The-Loop.d800024-c45.Car-Rental-Guide-Suppliers) - [Book Hotels with a Pool in Chicago on Expedia.com ](https://www.expedia.com/Chicago-Hotels-Hotel-With-Pool.0-0-d178248-tHotelwithPool.Travel-Guide-Filter-Hotels)