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 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-10&endDate=2025-10-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-11&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6132399&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next 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) ## 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/8000000/7820000/7818200/7818107/95a0afba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wheeler Mansion Near South Side 10/10 Exceptional (2) "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) ![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) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/2e0ab6dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency McCormick Place Chicago Near South Side 9.0/10 Wonderful (1004) "Excellent stay!" CA $335 CA $426 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=2025-10-25&endDate=2025-10-26®ionId=6132399&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Top Near South Side Hotel Reviews ![Holiday Inn Chicago Dwtn - The Mart by IHG](//images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344_y.jpg) ### Holiday Inn Chicago Dwtn - The Mart by IHG 10/10 Excellent "Great hotel - great location. It's a bummer that the view from the restaurant/bar isn't as cool as it used to be, because of the new buildings in front of it, but it's still pretty - and the drinks and food are very good. Room was very nice and clean. " [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "The onsite parking is worth the money compared to other lots. Walk where you can. The Embassy is in the perfect location for a lot of attractions." [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.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 "We stayed here for two nights, and I would definitely stay again. It is located next to the Cadillac Palace theater, and about a block from the Wells and Washington L stop. It was easy to take the train around the city, or walk to beautiful city views and great restaurants. The staff was friendly, the room was clean and quiet. Great for a weekend in Chicago!" [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.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 "This was definitely the perfect choice to stay " [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Hyatt Regency Chicago](//images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Lovely hotel" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![The Chicago Hotel Collection - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg) ### The Chicago Hotel Collection - Magnificent Mile 10/10 Excellent "Everything was" [](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Hotel was nice. Good area in walking distance to a lot of fun places and stuff to do. Staff was very nice. Only negative they charge for water bottles….which I think is crazy. Hotels should at least give 1 or 2 complimentary waters…. It’s water we are traveling. I understand charging after that. Also charged for checking in early. Just seemed like a lot of fees but overall was a good stay." [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "This was our 3rd time staying here in 6 months. As always…excellent experience! " [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![The Wade](//images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "Right across the street from the navy pier! Everything about the hotel is amazing as far as the lobby, weight room, pool, and room. The only thing that wasn’t good was the beds themselves. The weren’t comfortable. Other than that great place to stay." [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.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)