Title: Book the Best ADVENTURE Hotels in South Side in 2025 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26577-Museum-Of-Science-And-Industry.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels & Resorts for Couples in South Side, IL from CA $229 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 Hotels & Resorts for Couples Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-09-27&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-09-28&endDate=2025-09-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Hotels & Resorts for Couples ![City view](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/64dd2430.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/90000/84800/84736/d8be0ff0.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) ### Hyatt Regency McCormick Place Chicago Near South Side 9.2/10 Wonderful (1035) "Excellent stay!" CA $375 CA $473 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-McCormick-Place.h84736.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/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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/79f898c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Grant Park Hotel Downtown Chicago 8.2/10 Very good (2661) "Convenient location, friendly and helpful staff, nice bakery and restaurant attached to the hotel" CA $195 CA $229 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/28814a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/0fb0f5ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Living room](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/8ed533e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jaslin Hotel Chinatown 8.8/10 Excellent (1177) "Amazing location, super nice staff! " CA $262 CA $308 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/6d23e5ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/7fc8cfc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/ac7b16dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/19000000/18180000/18179000/18178914/c5fb01f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marriott Marquis Chicago Near South Side 9.2/10 Wonderful (1035) "Hotel was beautiful stayed for a concert and will come back sometime and stay again!!!" CA $458 CA $587 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Chicago-Hotels-Marriott-Marquis-Chicago.h18178914.Hotel-Information) ![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) ![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 (2) "A unique place to stay near the convention centre. " [](https://www.expedia.ca/Chicago-Hotels-The-Wheeler-Mansion.h7818107.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=2025-10-11&endDate=2025-10-12®ionId=553248635074842823&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Jaslin Hotel](//images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Was a great alternative to the big city when we went to see Sox. Property was clean, staff friendly. " [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Hyatt Place Chicago-South/University Medical Center](//images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "We enjoyed being able to go to restaurants and bars within walking distance " [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chicago Marriott Midway](//images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Quie" [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Carlton Inn Midway](//images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "Convenient " [](https://expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ## Explore a world of travel with Expedia - 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