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 [Nov 15 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-15&endDate=2025-11-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Nov 16 - Nov 17](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-16&endDate=2025-11-17&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-21&endDate=2025-11-23&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976475403&startDate=2025-11-28&endDate=2025-11-30&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Southwest Side Luxury Hotels ## Top Southwest Side Hotel Reviews ### Freehand Chicago 10/10 Excellent "Super friendly and helpful staff, environment felt warm and welcoming. The people who stay there are pretty cool as well! Rooms were clean and cozy. Would definitely stay there again if I’m in Chicago again." [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ### Eurostars Magnificent Mile 10/10 Excellent "The staff was so helpful and friendly!!!! " [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ### The Wade 10/10 Excellent "Staff was welcoming! We appreciated the engineering team for stepping in and helping us out! He was kind. Would stay again! " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "The customer service top tier!!! The rooms were extremely small but they were clean. Staff was very helpful. " [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Centrally located by the Magnificent Mile. Plenty of shopping options. Access to both train and bus public transportation. Hotel is older but kept. Staff are friendly, efficient, abd aware of comings and goings. Always greeting you ss you leave snd return. Rooms and property are clean. Rooms are spacious for a large metro city. I have stayed at this location multiple times. Will always be my first choice. " [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ### Hilton Chicago 10/10 Excellent "It was the swankiest joint I ever strayed in! I upgraded for $40 and had a room with a view of Lake Michigan! They had three restaurants/bars right in the hotel!!" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Clean room. Super friendly front desk staff. Complimentary drinks were a big plus! Whole property was amazing. Walking distance to everything. " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ### Warwick Allerton - Chicago 10/10 Excellent "Great" [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Beautiful hotel" [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in South Englewood](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Cheap-Hotels.0-n6132347-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Archer Heights](https://www.expedia.ca/Archer-Heights-Chicago-Hotels-Hotels-With-Free-Parking.0-n6132347-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - 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