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 ![](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 Hotels & Resorts for Couples Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Hotels & Resorts for Couples ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/3dbc8b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/98e3ca35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/e8f8e393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG Bedford Park 9.0/10 Wonderful (1151) "nice spacious clean rooms - several restraunts / fast food / stores nearby" CA $156 CA $183 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Living room](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/e921e6b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chic 3 BR CONDO](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d323a9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/273b53b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/4769286c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House Bronzeville 8.4/10 Very good (70) "Very convenient for a short term stay with private area and clean shared spaces the parking is very convenient as well" CA $93 CA $159 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, free cribs/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/64c4029a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/5496cb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/dd081548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG Downtown Chicago 8.8/10 Excellent (3218) "Great stay " CA $224 CA $262 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w2559h3837x0y3-191558cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w2560h3837x0y3-423017d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/95b10764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/bda30653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thompson Chicago, by Hyatt Downtown Chicago 9.2/10 Wonderful (1252) "Expensive, but comfortable and in a great location " CA $219 CA $299 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/7012a512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/a07d9bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/9cc7a10c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Chicago Dwtn - The Mart by IHG Downtown Chicago 8.8/10 Excellent (1943) "Very Nice Hotel in a great location." CA $220 CA $259 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/4e2c019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/da2c2cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/w3839h3333x0y0-56c69498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/4b5f6826.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical Downtown Chicago 8.4/10 Very good (2195) "Very clean accommodations and great customer service from the staff!!" CA $174 CA $204 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/6dfbfa42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/12c82a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/bf403e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, River View | View from room](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/c80457b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L7 Chicago by LOTTE Downtown Chicago 9.6/10 Exceptional (3095) "Great hotels " CA $278 CA $327 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view from property](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/2b1c0fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d2b26aad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Felix River North/Magnificent Mile Downtown Chicago 8.2/10 Very good (2283) "Great stay and great location " CA $113 CA $176 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/0ae99f9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Mediterranean cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/1145f7d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/36bc94a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; Mediterranean cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/24000/23963/c8d0f7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Talbott, Autograph Collection Downtown Chicago 9.4/10 Exceptional (39) "We were there for a Bachelorette party and the hotel was at a great location for it! We could walk to so many nice restaurants and shops! The hotel staff was super friendly as well! " CA $250 CA $328 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-The-Talbott-Hotel.h23963.Hotel-Information) ![Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/a8fb5620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/a5ba4cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/98cc37df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kinzie Hotel Downtown Chicago 9.2/10 Wonderful (1938) "Amazing location" CA $226 CA $320 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-Kinzie-Hotel.h992500.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=2025-10-31&endDate=2025-11-01®ionId=553248635074842823&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![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 "Pool needs some improvement, also water is a bit cold " [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Jaslin Hotel](//images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Excellent " [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Chicago Marriott Midway](//images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "No comment " [](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 "C L E A N" [](https://expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ## Explore a world of travel with Expedia - 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[Luxury Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Luxury-Hotel.0-n117842-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Oceanfront-Hotels.0-n117842-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Pet-Friendly-Hotel.0-n117842-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Spa-Hotel.0-n117842-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hyde Park Hotels](https://www.expedia.ca/Hyde-Park-Chicago-Hotels.0-n117842-0.Travel-Guide-Filter-Hotels) - [Hotels near Hyde Park Hair Salon](https://www.expedia.ca/Hyde-Park-Hair-Salon-Hotels.0-l553248621533116334-0.Travel-Guide-Filter-Hotels) - [Hotels near Ida B Wells House](https://www.expedia.ca/Ida-B-Wells-House-Hotels.0-l553248621533116338-0.Travel-Guide-Filter-Hotels) - [Vacation Homes in Indiana Station](https://www.expedia.ca/Indiana-Station-Private-Vacation-Homes.d6211032-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Cheap Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Cheap-Hotels.0-n6132343-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Luxury-Hotel.0-n6132343-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Kenwood](https://www.expedia.ca/Kenwood-Chicago-Hotels-Spa-Hotel.0-n6132343-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Kenwood Hotels](https://www.expedia.ca/Kenwood-Chicago-Hotels.0-n6132343-0.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Romantic-Hotel.0-n800025-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Waterpark-Hotels.0-n800025-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - 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[Hotels near University of Chicago](https://www.expedia.ca/University-Of-Chicago-Hotels.0-l6064081-0.Travel-Guide-Filter-Hotels) - [Hotels near University of Chicago Medicine](https://www.expedia.ca/University-Of-Chicago-Medicine-Hotels.0-l553248635389801569-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n171466-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Boutique-Hotel.0-n171466-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Cheap-Hotels.0-n171466-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Luxury-Hotel.0-n171466-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Washington Park Hotels](https://www.expedia.ca/Washington-Park-Chicago-Hotels.0-n171466-0.Travel-Guide-Filter-Hotels) - 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[Visit Indian Village](https://www.expedia.ca/Chicago-Indian-Village.dx553248635976382922) - [Chicago Museum of Science and Industry](https://www.expedia.ca/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction) - [Obama's House](https://www.expedia.ca/Obamas-House-Kenwood.d553248621533116333.Vacation-Attraction) - [Robie House](https://www.expedia.ca/Robie-House-Hyde-Park.d6064059.Vacation-Attraction) - [Car rentals near Hyde Park](https://www.expedia.ca/Car-Rentals-In-Hyde-Park.d117842.Car-Rental-Guide) - [Hertz Rental Cars in Hyde Park](https://www.expedia.ca/Hertz-Car-Rentals-In-Hyde-Park.d117842-c40.Car-Rental-Guide-Suppliers) - [Book Hotels & Resorts for Couples in South Side on Expedia.com](https://www.expedia.com/South-Side-Hotels-Couples-Resorts-Hotels.0-0-d553248635074842823-tCouplesResortsHotels.Travel-Guide-Filter-Hotels)