Title: Book the Best South Side LUXURY Hotels - Upscale Hotels in South Side, IL | Expedia.ca [South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.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 South Side Luxury Hotels Tonight [Feb 4 - Feb 5](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-04&endDate=2026-02-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Feb 5 - Feb 6](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-05&endDate=2026-02-06&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-13&endDate=2026-02-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for South Side luxury hotels ![Interior](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/18dd5e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Suite, 1 Bedroom](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/896f58e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/bf7253c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/w3908h6229x0y7-cf0011db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wheeler Mansion [](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information) Near South Side 9.0/10 Wonderful (4 reviews) "A unique place to stay near the convention centre. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leonardo [](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/a243f0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/79f898c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/b9d3aa50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/c33b753e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Grant Park Hotel [](https://www.expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) Downtown Chicago 8.2/10 Very good (2,667 reviews) "Clean room and the staff are great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Doug CA $98 CA $115 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/bc1f3373.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/1000000/90000/84800/84736/c441515d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/914fc3c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/d8be0ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency McCormick Place Chicago [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) Near South Side 9.2/10 Wonderful (1,065 reviews) "The room and staff were great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ivan CA $258 CA $335 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/099e5443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/e0a46a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shared fridge, microwave](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/e7d4b5da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/6a793d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chinatown Hotel Chicago [](https://www.expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) Chinatown 5.4/10 (1,000 reviews) "Great for roding the cta" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $80 CA $94 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.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=2026-02-19&endDate=2026-02-20®ionId=553248635074842823&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg) ### Holiday Inn Chicago – Midway Airport S by IHG 10/10 Excellent "Clean and cozy room guaranteed comfortable living. Unfortunately, there’s no microwave in the room. All the rest is fine. " [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Great rooms With upgraded, Recently Renovated! " [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "Staff was amazing! Chuck at breakfast was the absolute best. Can’t say enough about how great of a job he did to make us feel welcomed." [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Spent a night! Wish I could have stayed longer. The space was clean and beautifully designed, and the hotel staff were extremely accommodating to my needs. Wish I had gotten to enjoy the menu items, but I had to get back to the airport. The shuttle was also great; it came every 20 minutes, and I loved saving money on ride-sharing back to the airport in the morning. Overall great! " [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "Courteous staff. Clean rooms." [](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "It is a good place to stay." 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