Title: South Side Vacation Rentals from CA $248: Short-Term Rentals for 2025 | 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)[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) # South Side Vacation Rentals ![](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 Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-13&endDate=2025-10-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-14&endDate=2025-10-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [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) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in South Side ![Classic Apartment | Private kitchen](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/65b6e2ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment | Living area](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/2b79b031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/w2571h1446x1y1-ccdca671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Apartment | Bathroom](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/15271305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Apartment near Chicago Downtown Bridgeport CA $272 CA $476 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Chicago-Hotels-Stylish-Apartment-Near-Chicago-Downtown.h119973593.Hotel-Information) ![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/2c5edc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/0a34dfde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/77ca5eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/ac888596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio in Hyde Park-Walk to Lake & University Hyde Park 9.0/10 Wonderful (7) "This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. " CA $111 CA $248 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Studio-In-Hyde-Park-Walk-To-Lake-University.h116792603.Hotel-Information) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/de22ad61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/b97e6643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/dae3dcce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/0149089d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 1BR in Historic HydePark Hyde Park 7.6/10 Good (4) "The location couldn't be beat. The beds were super comfortable and the room was perfect for my husband and I. We'll definitely stay here again!" CA $111 CA $262 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-In-Historic-HydePark.h116793085.Hotel-Information) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/4efcd15b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/cc47c33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/829bcf7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/d10b773f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Studio Near UChicago Hyde Park 10/10 Exceptional (6) CA $111 CA $248 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Chicago-Hotels-Modern-Studio-Near-UChicago.h116793083.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/985b1568.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/2ebc6ff0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/79435de4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/d21ef160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright & Cozy 1BR Near UChicago Hyde Park 10/10 Exceptional (1) "This stay was very pleasant. The place was clean and the area safe. They provided two towel sets, dishware set, pans, utensils, cups, mugs, and coffee. Also a travel crib. I will definitely be back to show my littles the city. The apartment is located on the third floor. However the elevator is out of service. So if you’re handicapped I would not recommend this place. We however didn’t mind the haul upstairs three flights. It was very short and very few steps. We had packed light as we only... CA $111 CA $262 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Chicago-Hotels-Bright-Cozy-1BR-Near-UChicago.h116793062.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/853ce9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/95fddc46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/aa345e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/104000000/103950000/103943300/103943206/e32db205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Home Away From Home! Calumet Heights 9.6/10 Exceptional (12) "Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. " [](https://www.expedia.ca/Chicago-Hotels-A-Home-Away-From-Home.h103943206.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/a4c1202d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/bd8f40a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/0e90abd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/ec4a8eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Retreat: Cozy 1BR Apartment Hyde Park 10/10 Exceptional (3) "Our stay was very nice, with simple checkin / check out, and excellent communication by our host. " CA $111 CA $262 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Chicago-Hotels-Chic-Retreat-Cozy-1BR-Apartment.h116792510.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/7486dedf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/w2686h2011x2y3-3f3595f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/w1320h1248x0y1-c2adfd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/40a5fa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-12 guests Bridgeport 9.4/10 Exceptional (18) "The owners were SUPER helpful and their communication was SUPERB!" [](https://www.expedia.ca/Chicago-Hotels-Elegant-Mayors-Manor-In-Central-Chicago-9-Beds.h94721307.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) ![Marina](https://images.trvl-media.com/lodging/102000000/101330000/101326400/101326333/352970ba.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) ### 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) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/b84b9af4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/c2f1c810.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/5a5871f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/b621d6b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright & Spacious 2BR– Prime Hyde Park Location Hyde Park 4.0/10 (1) "My son and I were disappointed and didn't enjoy the stay because: 1) apartment windows are not noise proof from the street noise, 2) AC is noisy, 3) kitchen sinks and dish washer water clogged when we check in on Sep 15th. Building mgmt didn't get to resolve the clogging issue until Sep 17th afternoon. Two good thing about this apartment are 1) it is close to ME station and within walking distance to shopping and restaurants, 2) two bedrooms with king size bed." CA $126 CA $319 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Bright-Spacious-2BR-Prime-Hyde-Park-Location.h116792638.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119210000/119200900/119200890/3956f2e1.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/120000000/119210000/119200900/119200890/d9c5bca8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119210000/119200900/119200890/eedfc812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119210000/119200900/119200890/31a08ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4-bedroom apartment in marvelous Chicago with Workout Mirror, AC Bronzeville 10/10 Exceptional (1) "Very quiet street and easy access to Soldier Field. The property was spacious and was able to accommodate the needs of our family. The only concern was my inability to operate all the TVs but other than that i highly recommend this unit. " [](https://www.expedia.ca/Chicago-Hotels-4-Bedroom-Apartment-In-Marvelous-Chicago-With-Lululemon-Mirror.h119200890.Hotel-Information) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/f3e50bcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/fc07c1c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/8074f855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/6dd78f04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Charm Studio Apt in Chicago Hyde Park 10/10 Exceptional (1) CA $111 CA $248 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Charm-Studio-Apt-In-Chicago.h117124263.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/c0eeff3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/76d7780b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Hulu, streaming services](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/5cf813ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/f473e16f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! Greater Grand Crossing 8.0/10 Very good (10) "Came for a concert, enjoyed sight seeing. Apartment was a nice place to stay." [](https://www.expedia.ca/Chicago-Hotels-Comfy-4-Bedroom-Apartment-In-The-Center-Of-CHICAGO-15-Mins-From-Downtown.h73639173.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/b02b60ef.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) ![Interior](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/b96a4021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit. Woodlawn 7.4/10 Good (3) "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, 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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/8a220ed3.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) ![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) ### 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) ![Microwave](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/16ff56fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/1050258f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/4e885a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/5d21d940.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago Bronzeville 9.8/10 Exceptional (13) "Served us well for our event near the McCormick Center. Hospitality was second to none! " [](https://www.expedia.ca/Chicago-Hotels-Cozy-1-Bedroom-Apartment-With-WiFi.h107094905.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/71000000/70960000/70954100/70954028/53bddaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70960000/70954100/70954028/6de17961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/71000000/70960000/70954100/70954028/532c1b19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/71000000/70960000/70954100/70954028/0f2674a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now! Bronzeville 8.6/10 Excellent (14) "We will not be strangers to this spot in the future , our stay was comfortable and nothing was missed ! " [](https://www.expedia.ca/Chicago-Hotels-Luxury-Apartment-In-Bronzeville.h70954028.Hotel-Information) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/c2a9aa18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/f1d85784.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/95d170d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/4f2fb0ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio in Chicago Hyde Park CA $111 CA $248 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Chicago-Hotels-Cozy-Studio-In-Chicago.h116792582.Hotel-Information) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/7e0b7a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/f0b2b35a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/w1196h800x4y0-66d9df7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/0b1f4ad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trendy Studio Apartment in Chicago Hyde Park CA $111 CA $248 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Chicago-Hotels-Trendy-Studio-Apartment-In-Chicago.h116792613.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/00485267.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/c4cab1c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/efac9f0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/4a26d943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay, Relax & Explore Chicago Greater Grand Crossing 9.0/10 Wonderful (2) "Very nice property!" [](https://www.expedia.ca/Chicago-Hotels-Stay.h119426636.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=2025-10-27&endDate=2025-10-28®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-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals) ## 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 "Staff is accommodating friendly and professional. Keep up the excellent work. Location location location. This couldnt be a better location" [](https://expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.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 "Common areas are spacious and well kept. Room was sufficient with a bed and chair and clean. I was provided two bath towels and hand towels. Although unusual, sharing a common bathroom wasn’t an issue for me and the bathroom was kept clean. " [](https://expedia.ca/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.Hotel-Information) ![Admiral Motel By Oyo Chicago I-94](//images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b66dd193_y.jpg) ### Admiral Motel By Oyo Chicago I-94 6/10 Okay "Fine stay " [](https://expedia.ca/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) ![Sophy Hyde Park](//images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg) ### Sophy Hyde Park 10/10 Excellent "I did not sample the food or the gym as I was in town to attend a family wedding and related functions. " [](https://expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.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 "It was very pleasant" [](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 "nice spacious clean rooms - several restraunts / fast food / stores nearby" [](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 "Nice place to stay to catch a flight at midway airport " [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Jaslin Hotel](//images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "only the shower floor grout looked dirty so i bought slippers in China town. Everything else was perfect. Location for convention center parking and subway." [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.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 "Great hotel, great friendly staff" [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ## Find out more about South Side **Everything you need to know about** **South Side** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Side vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **South Side vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in South Side. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Side vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Side vacation rentals we have selected for you start as low as CA $248 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on South Side rentals** At Expedia, we put the best South Side vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top South Side rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Side vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in South Side ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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[Grant Park](https://expedia.ca/Grant-Park-Downtown-Chicago.d507389.Vacation-Attraction) General - [Flight Deals & Seat Sales](https://expedia.ca/flight-deals) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)