Title: South Side Guest Houses from CA $140 | 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) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 15 - May 17](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-05-15&endDate=2026-05-17&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side guest houses ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/5089d88a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/994a5eaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/18e8c92a.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 (84 reviews) "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 $136 CA $160 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/41972c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/4185cea1.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 [](https://www.expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) Bronzeville 8.6/10 Excellent (47 reviews) "Very good place,nice host " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Qiang CA $119 CA $140 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/3bf4676d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/8c07545e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/108000000/107230000/107226500/107226405/7263f497.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 [](https://www.expedia.ca/Chicago-Hotels-Chicago-Avenue-Inn.h107226405.Hotel-Information) Humboldt Park 7.0/10 Good (101 reviews) "plenty of street parking " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurel CA $70 CA $194 total includes taxes & fees Apr 8 - Apr 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=2026-04-05&endDate=2026-04-06®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 ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/e8f8e393_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 8/10 Good "Good front desk" [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.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 6/10 Okay "The tv didn’t work, the toilet ran non stop, and the bathroom door wouldn’t shut completely. We also had to wait until 515 to check in!" [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f1fd01e1_y.jpg) ### Sophy Hyde Park 10/10 Excellent "Exceptional property; well maintained; great atmosphere " [](https://expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Clean room Convenient location " [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg) ### SpringHill Suites by Marriott Chicago Chinatown 10/10 Excellent "We were happily surprised at how nice the hotel room was! And parking felt secure. Breakfast was great. " [](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/099e5443_y.jpg) ### Chinatown Hotel Chicago 8/10 Good "It was a room" [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/b32fc0e7_y.jpg) ### Motel 6 - Chicago, IL 4/10 Poor "When you book with a motel, you know you’re not getting a five star experience. This was no exception. The first room we were given was filthy; dirt was all over the floor and it smelled strongly of smoke (despite being a non-smoking room). We requested a different room, which they didn’t give us any hassle about. The second room was cleaner and smelled less of smoke. However, the smell of stale cigarettes still lingered in the second room (which made sense considering the cigarette burns in the walls and bathroom). While the bed in both rooms looked clean (and appeared to not have any bedbugs), the walls and floor were filthy and looked as though they had never been cleaned. The towels were threadbare and scratchy, and I don’t think I’ve seen older pillows in my life. It reminded me of the crappy apartments I’ve previously lived in, except they didn’t even bother with the landlord paint job. The heater did work (but also smelled like smoke and mildew); we didn’t try the A/C since it’s March in Chicago. There’s not much around the area, but there are 4 gas stations and a bus stop a block away, so it’s not hard to get to some place better. Bottom line, would you die staying the night here? No. Should you stay somewhere else if you have the means? Yes. " [](https://expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Saratoga Motel By Capital O Near Midway Airport Chicago IL](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3456h2300x0y0-6e038619_y.jpg) ### Saratoga Motel By Capital O Near Midway Airport Chicago IL 2/10 Terrible "This hotel was an absolute disaster, and the entire experience left my girlfriend and me feeling grossed out, frustrated, and genuinely unsafe. The rooms were far from clean—every single one had visible mold in the bathroom: black patches and spots covering the grout, shower tiles, wall edges, and caulking. It looked like years of neglect, even without any obvious smell. I had to switch rooms three times because each one was a new level of unacceptable: • First room: Mold in the bathroom + in-room jacuzzi jets completely non-functional (hit the switch multiple times—dead silence, no jets, no bubbles, nothing). • Second room: Refrigerator stopped working entirely (stayed warm inside, wouldn’t cool, ruined anything we tried to store in it). • Third room: Still terrible—the sheets clearly hadn’t been changed properly (hairs on the pillow, sticky residue on the nightstand), there were burn marks/scorch marks on the sheets (like cigarette burns or iron mishaps that were never replaced), and no latch, chain, or secondary lock on the door (just the basic knob lock, offering zero extra security). The most horrifying incident happened around 6 a.m. one morning: We were both fast asleep, completely naked, when I woke up just in time to see someone (likely staff or someone with access) quietly slipping out of the room and closing the door behind them. I was in shock, didn’t immediately yell or jump up—I just froze watching them leave. My girlfriend slept through it and heard nothing." [](https://expedia.ca/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information) ![Villa Dubois Guest House](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1_y.jpg) ### Villa Dubois Guest House 6/10 Okay "Quaint and quiet for solo travelers. A pretty cozy stay but be very cautious of the refundable deposit. They’re not on it like your average hotel/airbnb so you will have to remind them via email. Their phone number isn’t the greatest, as it is hard to communicate to the staff, they don’t have a regular set of hours by the phone. Kitchen wasn’t used for my stay but it looked neat and clean, perfect for those who intend on staying longer. " [](https://expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ## Find out more about South Side ## South Side Guest Houses information | Number of reviews | 232 | | ----------------- | -------------- | | Accommodation | 3 Guest Houses | | Lowest Price | CA $140 | | Highest Price | CA $194 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [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) - [Luxury Hotels in Bronzeville ](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Bronzeville Hotels ](https://www.expedia.ca/Bronzeville-Chicago-Hotels.0-n6132245-0.Travel-Guide-Filter-Hotels) - [Canaryville Hotels ](https://www.expedia.ca/Canaryville-Chicago-Hotels.0-n6132307-0.Travel-Guide-Filter-Hotels) - 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