Title: Book the Best Southwest Side LUXURY Hotels - Upscale Hotels in Southwest Side, IL | Expedia.ca [Southwest Side Travel Guide](https://expedia.ca/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.ca/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.ca/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide)[Southwest Side Vacation Packages](https://expedia.ca/Southwest-Side.d553248635976475403.Destination-Travel-Guides) ![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by by Midway Intl Airport # Find luxury hotels in Southwest Side, IL - ![](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 Southwest Side Luxury Hotels Tonight [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-14&endDate=2025-12-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-15&endDate=2025-12-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Southwest Side Hotel Reviews ![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 "Hotel was very nice. Clean and quiet rooms. Good value for the price. Staff was super friendly and overly accommodating during our stay. From the curb service upon arrival, the maintenance man that had to make a minor repair in our room to the bellman that waited at the curb with us to load our bags in the uber. Cannot recommend this hotel enough!" [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.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 "Beautiful old hotel convenient to downtown . Wonderful rooms and great onsite dining. You can hear the trains outside from pretty much every room but I found it acceptable noise level. " [](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "The staff was amazing and our room was just as good. Can’t wait to come back!" [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "The room view was beautiful! The staff was super attentive and helpful. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Everything was wonderful. We did not have breakfast" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.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) ![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "Great location" [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.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) ![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 "We loved the hotel, parking was a bit of a ways off." 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