Title: South Side Condo Rentals | 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 Condos Rentals in South Side ![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 In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select South Side Condo Rentals ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104350000/104341900/104341807/6f199fbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/105000000/104350000/104341900/104341807/84d1a57d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104350000/104341900/104341807/52ba7bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/105000000/104350000/104341900/104341807/cf0e0bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Condo-Obama & University of Chicago Area Woodlawn 8.8/10 Excellent (13) "I thought this place was so cute, loved the outset deck! Was spacious and the host was very nice and helpful when needed! Would stay again for sure! " [](https://www.expedia.ca/Chicago-Hotels-Modern-Condo-Obama-University-Of-Chicago-Area.h104341807.Hotel-Information) ![Fridge, microwave, oven, coffee/tea maker](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/699a08a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/d14727bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/147b77ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/5349db93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable Condo in the Heart of Bronzeville by RedAwning Bronzeville 7.2/10 Good (5) "There was confusion with VRBO regarding our arrival date, no fault of the property owner. They made arrangements to clean the unit and provide lunch for our group while we waited and offered a second night free for the inconvenience. Highly recommend. Property owner went above and beyond!" [](https://www.expedia.ca/Chicago-Hotels-Comfortable-Condo-In-The-Heart-Of-Bronzeville-By-RedAwning.h103276998.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/94000000/93390000/93385800/93385751/6ea890f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93390000/93385800/93385751/9492f9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93390000/93385800/93385751/bf22d15b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/94000000/93390000/93385800/93385751/5148121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions Bronzeville 8.2/10 Very good (10) "We found the place to be extremly clean and comfortable . Its really close to down town and great resturants. Definetly would book again ." [](https://www.expedia.ca/Chicago-Hotels-Bright-2-Bed2-Bath-Condo-With-Patio-Less-Than-10-Mins-From-Major-Attractions.h93385751.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/00965c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/c329dc83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/5058bb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117800000/117794900/117794818/e8046086.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly Chicago 10/10 Exceptional (1) "Clean apartment and great communication with host. Fixed any small problems very quickly. " [](https://www.expedia.ca/Chicago-Hotels-South-Shore-Chicago-Condo-1-Block-To-Lake-WiFi-AC-Elevator-420-Friendly.h117794818.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107610900/107610850/11a06bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107620000/107610900/107610850/eb349ae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/108000000/107620000/107610900/107610850/d0556cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107620000/107610900/107610850/9f88264e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-bedroom condo next to Chicago Midway International Airport Garfield Ridge 10/10 Exceptional (9) "super nice place!" [](https://www.expedia.ca/Chicago-Hotels-1st-Floor-1-Bedroom-Condo-Close-To-Chicago-Midway-International-Airport.h107610850.Hotel-Information) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/111000000/110380000/110370800/110370757/76e490a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110380000/110370800/110370757/9c16a503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors](https://images.trvl-media.com/lodging/111000000/110380000/110370800/110370757/36a88c0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110380000/110370800/110370757/eb8bf008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful, modern 3 bed 2 bath condo near Hyde Park, Obama Center and Lakefront South Shore 10/10 Exceptional (4) "Great property! Host was super nice and accommodating. Will definitely stay again " [](https://www.expedia.ca/Chicago-Hotels-Beautiful.h110370757.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/93000000/92280000/92279900/92279889/635e6ede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/93000000/92280000/92279900/92279889/3d713fd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/93000000/92280000/92279900/92279889/8fb1e353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/93000000/92280000/92279900/92279889/0fba439d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bronzeville Manor walking distance to hospitals Bronzeville 9.8/10 Exceptional (18) "Great location, very clean place. Ample street parking and the owner is very nice. I’ll definitely be booking this location again." [](https://www.expedia.ca/Chicago-Hotels-Bronzeville-Manor-Walking-Distance-To-Hospitals.h92279889.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/116000000/115930000/115925300/115925246/3de8e55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright Vintage U of C Center Condo with WiFi, AC in enjoyable Chicago Woodlawn "They went out of the way to make sure we had keys to get in and got in early since no one was there night before." [](https://www.expedia.ca/Chicago-Hotels-Bright-Vintage-U-Of-C-Center-Condo-With-WiFi.h115925246.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89809500/89809470/057afebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89810000/89809500/89809470/d8bfe102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/90000000/89810000/89809500/89809470/28c9e526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89810000/89809500/89809470/b374c27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious two bedroom condo with a cozy feel! Essex 8.8/10 Excellent (6) "Wonderful beach house. Plenty of room and very close to the beach. The owner is very quick to respond if you have questions or concerns" [](https://www.expedia.ca/Chicago-Hotels-Spacious-Two-Bedroom-Condo-With-A-Cozy-Feel.h89809470.Hotel-Information) ![Fridge, microwave, coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/67000000/66700000/66698500/66698407/bd91e8c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/67000000/66700000/66698500/66698407/7aa7fc6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66700000/66698500/66698407/7ce11e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66700000/66698500/66698407/c10dd13d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena Chinatown 9.6/10 Exceptional (26) "Two women colleagues. We each had our own bathroom, plus kitchenette for far less money than a hotel room. Clean and close to McCormick Place." [](https://www.expedia.ca/Chicago-Hotels-3-3A-3-Bedroom-Condo-W-Parking-Chinatown.h66698407.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66910000/66900400/66900347/w905h683x60y0-8fe95f7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/67000000/66910000/66900400/66900347/w905h683x60y0-8354abf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/67000000/66910000/66900400/66900347/w905h683x60y0-a5edb361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/67000000/66910000/66900400/66900347/af9bba9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 #1N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown Armour Square 9.0/10 Wonderful (11) "We enjoyed the apartment. It was clean, had enough bath towels and soaps . The beds were comfortable and the bed linens were comfortable. Each bedroom having their own bathroom was a real bonus. the CTA stop was a fairly short walk. Their we re a lot of places to eat that were within walking distance., The kitchen needed more supplies such as dish towels, mixing bowl and spatula. Enjoyed the stay, would stay again if the need arises." [](https://www.expedia.ca/Chicago-Hotels-4-1N-4-Bedroom-4-Bath-Condo-McCormick-Place.h66900347.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102420000/102412100/102412091/cc35a208.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102420000/102412100/102412091/cbbb40b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102420000/102412100/102412091/6e33824a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/103000000/102420000/102412100/102412091/f370b1f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Stay on UChicago Campus 11 min walk to hospitals Woodlawn 10/10 Exceptional (7) "Our family stay was wonderful! The property was great, the owners were available and courteous. " [](https://www.expedia.ca/Chicago-Hotels-Modern-Lux-Stay-On-UChicago-Campus-11-Min-Walk-From-CCD-And-Mitchell-Hospitals.h102412091.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/032f24a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/5e65af9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/bcd8e308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/7b79eb91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chic Urban Oasis Near the Lake! South Shore 8.0/10 Very good (7) "Everything about the host and stay was amazing this will be my go to spot for my family and me" [](https://www.expedia.ca/Chicago-Hotels-The-Chic-Urban-Oasis-Near-The-Lake.h101326333.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/8b761903.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/b96a4021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/a43ffef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/defd0847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit. Woodlawn 10/10 Exceptional (2) "The house was absolutely beautiful ! Very spacious and nice! Comfy beds and clean. " [](https://www.expedia.ca/Chicago-Hotels-Modern-Duplex-Obama-University-Chicago-Area-3BR.h105642745.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66940000/66937900/66937849/w905h683x60y0-bb093df2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/67000000/66940000/66937900/66937849/w1024h594x0y47-5f0d0654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/67000000/66940000/66937900/66937849/w906h683x59y0-6a9747e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/67000000/66940000/66937900/66937849/8ee9e375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 #2S - 5 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown Armour Square 9.6/10 Exceptional (13) "Everything was as advertised and super convenient for our group if 8. Highly recommended VRBO! " [](https://www.expedia.ca/Chicago-Hotels-4-2S-5-Bedroom-Condo-McCormick-Place.h66937849.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63120000/63110900/63110886/802cc877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63120000/63110900/63110886/6332bafc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/64000000/63120000/63110900/63110886/3fc60bed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, premium bedding, memory foam beds, desk](https://images.trvl-media.com/lodging/64000000/63120000/63110900/63110886/bab0f689.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 #3B - Modern 3 bedroom Condo - McCormick Place, Wintrust Arena, Chinatown Chinatown 9.6/10 Exceptional (27) "Good location and clean property." [](https://www.expedia.ca/Chicago-Hotels-3-3B-Modern-3-Bedroom-Condo-McCormick-Place.h63110886.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63950000/63945900/63945824/66f99539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/64000000/63950000/63945900/63945824/b2e004ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/64000000/63950000/63945900/63945824/1867f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/64000000/63950000/63945900/63945824/83917dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown Chinatown 10/10 Exceptional (13) "Our group of 16 people really enjoyed staying at this property. We were so close to everything, surrounded by great food amd shopping, we felt very safe, and the property manager was so responsive to us! We would recommended this property to any family or big group and will be staying here if we come back to Chicago!" [](https://www.expedia.ca/Chicago-Hotels-1-33-4-Bedroom-2-Bath-Condo-Near-McCormick-Place.h63945824.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69630000/69629200/69629109/w1078h724x8y0-58d6762b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/70000000/69630000/69629200/69629109/1e9cabc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/70000000/69630000/69629200/69629109/ba97a853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69630000/69629200/69629109/45b8b8f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cozy Nest: King Bed in Quiet and Safe Condo by McCormick Place and Midway! Washington Park 9.0/10 Wonderful (6) "Rough start getting into the place but once we got over anything we needed i would use this place again" [](https://www.expedia.ca/Chicago-Hotels-The-Cozy-Nest-King-Bed-In-Quiet-And-Safe-Condo-By-McCormick-Place-And-Midway.h69629109.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83630000/83627500/83627431/1833f469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83630000/83627500/83627431/f28fefc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83630000/83627500/83627431/f6561ba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83630000/83627500/83627431/5bcbf5c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A luxury vintage condo close to lakefront and minutes from downtown! South Shore [](https://www.expedia.ca/Chicago-Hotels-A-Luxury-Vintage-Condo-Close-To-Lakefront-And-Minutes-From-Downtown.h83627431.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/115000000/114390000/114381400/114381359/7dc748fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114390000/114381400/114381359/b90aab92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114390000/114381400/114381359/dc972503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114390000/114381400/114381359/dc4c1572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Parisian Retreat on University of Chicago Campus Woodlawn [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-Parisian-Retreat-On-University-Of-Chicago-Campus.h114381359.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=2025-10-15&endDate=2025-10-16®ionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation) ## Top South Side Hotel Reviews ![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 "It was close enough to the convention center that i could walk" [](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 "I love the staff! Courtesy, kind, and very professional " [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.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) ![Mccormick Place Guest House](//images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/b6c2dad6_y.jpg) ### Mccormick Place Guest House 10/10 Excellent "The Villa Dubois is very clean. Instructions were provided throughout the home and everything was self explanatory. The house is very spacious and provides privacy and amenities throughout the space. I enjoyed good nights rest and was only 5 minutes away from my business/church function. I highly recommend Villa Dubois. I will be back and look forward to renting again. " [](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 "Ok" [](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 "Close to the airport for those early flights." [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Chinatown Hotel Chicago](//images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "It's not a palace, but it's safe, clean and quiet. It's in Chinatown, a block and a half from the L stop. There are lots of restaurants and shops nearby." [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Chicago Marriott Midway](//images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Great service, love the amenities, easy to get to" [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.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 "Cool property, very safe with cams and code-locked door. No issues with noise, had a pretty quiet peaceful stay. Good parking situation, that’s something I was worried about but we never had problems parking. Unit is very close to transit lines. My girlfriend and I were out walking very late and never felt unsafe in this area. " [](https://expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ## Find out more about South Side ## South Side Condo Rentals information | Number of reviews | 155 | | --- | --- | | Accommodation | 52 Condo Rentals | | Lowest Price | | | Highest Price | | ## 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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