Title: South Side Guest Houses from CA $123 | 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) ![I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck. ](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Remington # Search Guest Houses in South Side from CA $123 - ![](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 prices for these dates Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select South Side Guest Houses ![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) ![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 Bronzeville 8.6/10 Excellent (77) "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 $105 CA $123 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Full-size fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/b6c2dad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/0aedd339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/c0e1e78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/dd3fd8f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mccormick Place Guest House Bronzeville 8.8/10 Excellent (46) "Very good place,nice host " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Qiang CA $105 CA $123 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/f37da67a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/19703ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/1c564c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/7bc87cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Avenue Inn Humboldt Park 7.0/10 Good (100) "It was a great experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $47 CA $165 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Avenue-Inn.h107226405.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=2025-12-17&endDate=2025-12-18®ionId=553248635074842823&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_553248635074842823) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Guest-Houses.d553248635074842823-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Guest-Houses.d553248635074842823-aaGuestHouses.Travel-Guide-Accommodation) ## Top South Side Hotel Reviews ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 10/10 Excellent "The need to stay in Chicago overnight was unplanned so finding the room clean and looking comfortable right away made my stress level come down" [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg) ### Sophy Hyde Park 10/10 Excellent "Very nice room and amenities. We enjoy the atmosphere in the lobby!!" [](https://expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.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! " [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg) ### Motel 6 - Chicago, IL 10/10 Excellent "Grest" [](https://expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Excellent- we were able to check out late for a small fee" [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![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 "As always fabulous experience. Great customer service." [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "Hotel and room was very clean and the desk clerk was courteous " [](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Saratoga Motel By Capital O Near Midway Airport Chicago IL](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3451h2304x0y0-39d39828_y.jpg) ### Saratoga Motel By Capital O Near Midway Airport Chicago IL 10/10 Excellent "Room was spotless " [](https://expedia.ca/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information) ![Best Motel By OYO Chicago I-90](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/19cdbb10_y.jpg) ### Best Motel By OYO Chicago I-90 8/10 Good "Clean room " [](https://expedia.ca/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) ## Find out more about South Side ## South Side Guest Houses information | Number of reviews | 218 | | --- | --- | | Accommodation | 3 Guest Houses | | Lowest Price | CA $123 | | Highest Price | CA $165 | ## Explore a world of travel with Expedia - 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