Title: Book the Best ADVENTURE Hotels in South Side in 2026 | 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) # Find Hotels & Resorts for Couples in South Side, IL from CA $120 - ![](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 [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-29&endDate=2025-12-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side adventure hotels ![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) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/f80081f8.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/1000000/210000/201300/201281/3dbc8b3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) Bedford Park 8.8/10 Excellent (1249) "Will definitely stay there again ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose Remedios CA $153 CA $180 total includes taxes & fees Dec 30 - Dec 31 [](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) ![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) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1.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) ### Villa Dubois Guest House [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) Bronzeville 8.6/10 Excellent (79) "My stay was very pleasant. The accommodation was comfortable, easily accessible, and well connected to public transport. I highly recommend it to anyone visiting the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lizeth CA $103 CA $120 total includes taxes & fees Dec 29 - Dec 30 [](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) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/dd081548.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) ![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/ddbd86a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) Downtown Chicago 8.8/10 Excellent (3523) "Really nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Saulius CA $159 CA $186 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/a07d9bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/481e5f5c.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) ### Holiday Inn Chicago Dwtn - The Mart by IHG [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.Hotel-Information) Downtown Chicago 8.8/10 Excellent (2070) "Really nice rooms at a good rate " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madelyn CA $146 CA $172 total includes taxes & fees Jan 15 - Jan 16, 2026 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Dwtn-Wolf-Point.h5467.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/1000000/10000/4200/4200/1272603a.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) ### L7 Chicago by LOTTE [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (3445) "Amazing place to stay and super accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carson CA $171 CA $200 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Chicago-Hotels-L7-Chicago-By-LOTTE.h4200.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) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/c5ba978a.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/w3839h3333x0y0-56c69498.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical [](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2306) "Excellent hotel. Loved staying there" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) cristina CA $135 CA $159 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w3837h2557x3y3-ef0f356b.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/95b10764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thompson Chicago, by Hyatt [](https://www.expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1305) "Love this hotel, right in the middle of a great area re: restaurants, bars, night scene, etc. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yoshio CA $185 CA $257 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Chicago-Hotels-Thompson-Chicago.h26076.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) ![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/279c3768.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) ![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) ### Hotel Felix River North/Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) Downtown Chicago 8.2/10 Very good (2481) "Decent hotel in a great location with extremely helpful staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/6b3ccd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed | Bathroom](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/6bab11c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/c08c8670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/870000/864300/864219/079d3f4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sofitel Chicago Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Sofitel-Chicago-Magnificent-Mile.h864219.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (2274) "Great hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shantasha CA $220 CA $298 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Chicago-Hotels-Sofitel-Chicago-Magnificent-Mile.h864219.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) ![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) ![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) ![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) ### Kinzie Hotel [](https://www.expedia.ca/Chicago-Hotels-Kinzie-Hotel.h992500.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (2033) "I liked the hospitality of the staff, and I felt that the location was pretty good! " ![South Korea](https://a.travel-assets.com/egds/marks/flags/kr.svg) KYOUNGJOO CA $132 CA $208 total includes taxes & fees Dec 29 - Dec 30 [](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=2026-01-11&endDate=2026-01-12®ionId=553248635074842823&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![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 "The staff was super friendly, and the room was clean! Great location." [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Staff was friendly and very helpful. Hotel was really clean" [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "Staff is great, clean rooms " [](https://expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Very convenient and clean and friendly! 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