Title: South Side Guest Houses from CA $83 | 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) # Search Guest Houses in South Side from CA $83 ![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 prices for these dates Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-09-26&endDate=2025-09-28&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select South Side Guest Houses ## Our top choices for South Side guest houses ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/f37da67a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/413d095f.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/f1aa0fea.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) ### Chicago Avenue Inn Humboldt Park 7.0/10 Good (90) "It's a good place if you was traveling with a group. That way your group would get the entire floor." CA $98 CA $182 total includes taxes & fees Sep 22 - Sep 23 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Avenue-Inn.h107226405.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 8.6/10 Excellent (65) "Very convenient for a short term stay with private area and clean shared spaces the parking is very convenient as well" CA $83 CA $146 total includes taxes & fees Sep 18 - Sep 19 [](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/dd3fd8f8.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) ### Mccormick Place Guest House Bronzeville 8.6/10 Excellent (27) "Beautiful decor, spotlessly clean " CA $88 CA $152 total includes taxes & fees Sep 18 - Sep 19 [](https://www.expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/w960h1278x0y0-858a683c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment - 3rd Floor | Private kitchen](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/fa373d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/89374e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment - 3rd Floor | Living area](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/0ac374cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigleyville Inn Lakeview 10/10 Exceptional (19) "Beautiful place to stay. Cooked some of our own meals. Kitchen was well stocked with even some condiments. Bottle water n beer were appreciated. Would stay there again. " CA $376 CA $641 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-Wrigleyville-Inn.h91438413.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=2025-10-01&endDate=2025-10-02®ionId=553248635074842823&adults=2&lodging=GUEST_HOUSE&sort=RECOMMENDED&openPlayBack=true) ![](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 ![Jaslin Hotel](//images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "The hotel was very nice. The room was very clean. the staff was very friendly. However, the exercise facility needs a major upgrade. There is a gross lack of quality equipment. In short, the gym needs a full assessment and a total makeover. Other than the gym, the Jaslin Hotel is a great place to stay. " [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Villa Dubois Guest House](//images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/e921e6b3_y.jpg) ### Villa Dubois Guest House 10/10 Excellent "I just felt like the deposit was too steep. I was willing to do 100 like most hotels, but I know it’s more like a Airbnb." [](https://expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Mccormick Place Guest House](//images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/b6c2dad6_y.jpg) ### Mccormick Place Guest House 10/10 Excellent "Beautiful decor, spotlessly clean " [](https://expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) ![Motel 6 - Chicago, IL](//images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg) ### Motel 6 - Chicago, IL 10/10 Excellent "Clean " [](https://expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](//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 "Staff is great. Did transportation with ride share and it was easy. Several different places to eat within walking distance." [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.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) ![SpringHill Suites by Marriott Chicago Chinatown](//images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg) ### SpringHill Suites by Marriott Chicago Chinatown 10/10 Excellent "Very nice, great breakfast and friendly staff. " [](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.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 "Loved it" [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ## Find out more about South Side ## South Side Guest Houses information | Number of reviews | 91 | | --- | --- | | Accommodation | 3 Guest Houses | | Lowest Price | CA $83 | | Highest Price | CA $88 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Explore a world of travel with Expedia - [Cheap Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Cheap-Hotels.0-n6132245-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Family-Hotel.0-n6132245-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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