Title: Book the Best Near South Side LUXURY Hotels - Upscale Hotels in Near South Side, Chicago | Expedia.ca [Near South Side Travel Guide](https://expedia.ca/Chicago-Near-South-Side.dx6132399)[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)[Near South Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-South-Side.d6132399.Car-Rental-Guide)[Near South Side Vacations](https://expedia.ca/Near-South-Side.d6132399.Destination-Travel-Guides) ![South Loop showing night scenes and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191954-South-Loop.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Luxury Hotels in Near South Side, Chicago ![](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 Near South Side Luxury Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-15&endDate=2025-10-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-16&endDate=2025-10-17&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-17&endDate=2025-10-19&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Near South Side Luxury Hotels ![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) ![Sports facility](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/09b5ecfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/95a0afba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/c6aa1dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wheeler Mansion Near South Side 10/10 Exceptional (3) "A unique place to stay near the convention centre. " [](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information) ![City view](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Asian cuisine](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/947219c2.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) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/df55aaa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency McCormick Place Chicago Near South Side 9.0/10 Wonderful (1012) "Excellent stay!" CA $336 CA $427 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.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=2025-10-29&endDate=2025-10-30®ionId=6132399&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Near South Side Hotel Reviews ![Crowne Plaza Chicago West Loop by IHG](//images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "Spent a night for our 14th anniversary. The staff was very thoughtful and kind. We appreciate the staff and room!" [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "This was perfect for Chicago Marathon. Good proximity to start and finish (about a mile) and was excellent location for spectating. " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "BEAUTIFUL IS ALL I HAVE TO SAY. THANKS SECURITY, I HAD A SAFE FUN FILLED DAY. LMAOOOO. Can't wait to return. " [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Breakfast was great! " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Excellent location for visiting Chicago, near major attractions, walking distance to mig mile and Chicago river. Subway station is beside the hotel. Many restaurants are around. Hotel is a little old but condition is good and the price is reasonable. Staffs are very friendly. " [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Clean rooms, great service." [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "The bell hops were awesome!! If i needed to know anything, all i had to do was ask them. " [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "This was the best hotel I ever stayed at! I did not want to leave. It was very clean and the cleaning staff was attentive and thorough. The staff at the desk were friendly and knowledgeable, and never acted disgruntled or impatient. The bellhops were excellent and trustworthy and anticipated our needs. The hotel was just beautiful and clean in the lobby with boutique atmosphere and art. The room was spacious with comfortable bed and furnishings. The coffee was excellent and the bathroom felt luxurious. We just loved everything! The restaurant food was great quality and not overpriced. And, our location downtown couldn’t be better, near Riverwalk and Michigan Avenue. We thoroughly enjoyed our stay. Thank you, Sonesta!" [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Clean.Comfortable beds. Great location .Includes a great breakfast." [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to Near South Side? > Known for its museums and skyscrapers, Near South Side also has some interesting things to see and do including Soldier Field and Lake Michigan, so you may want to take in the local sights during your visit. ### What's the best luxury place to stay in Near South Side? > [The Wheeler Mansion](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.Hotel-Information) is a luxury hotel with a terrace and a bar, and it's a popular choice for Expedia travelers looking for an elegant place to stay. ### What's there to see and do in Near South Side? > When you're in Near South Side, enjoy exploring the sights and attractions here including Soldier Field, Lake Michigan, and Wintrust Arena. If you have a little extra time during your trip, you might want to check out Northerly Island Natural Area and Arie Crown Theater. ### How can I get around Near South Side? > It's easier to get around town in style when you know your options. 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[Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Visit Downtown Chicago](https://www.expedia.ca/Chicago-Downtown-Chicago.dx6350699) - [Visit Prairie District](https://www.expedia.ca/Chicago-Prairie-District.dx553248635976473159) - [Visit South Loop](https://www.expedia.ca/Chicago-South-Loop.dx6130108) - [Visit The Loop](https://www.expedia.ca/Chicago-The-Loop.dx800024) - [Chicago Vacations](https://www.expedia.ca/Chicago.d178248.Destination-Travel-Guides) - [South Loop Vacations](https://www.expedia.ca/South-Loop.d6130108.Destination-Travel-Guides) - [Advantage Rent-A-Car Rental Cars in South Loop](https://www.expedia.ca/Advantage-Rent-A-Car-Car-Rentals-In-South-Loop.d6130108-c3.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Central Station](https://www.expedia.ca/Budget-Car-Rentals-In-Central-Station.d6132250-c39.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in South Loop](https://www.expedia.ca/Enterprise-Car-Rentals-In-South-Loop.d6130108-c15.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in South Loop](https://www.expedia.ca/Sixt-Car-Rentals-In-South-Loop.d6130108-c35.Car-Rental-Guide-Suppliers) - [Things to do in Chicago](https://www.expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) - [Book Hotels in Near South Side on Expedia.com](https://www.expedia.com/Near-South-Side-Chicago-Hotels-Luxury-Hotel.0-n6132399-0-tLuxuryHotel.Travel-Guide-Filter-Hotels)