Title: Holiday Rentals South Side from £121: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [South Side Travel Guide](https://expedia.co.uk/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Flights to South Side](https://expedia.co.uk/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide)[South Side Holidays](https://expedia.co.uk/South-Side.d553248635074842823.Holidays-City-Breaks) ![Chicago, IL featuring interior views and an airport as well as a couple](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by by Midway Intl Airport # Search Holiday Rentals in South Side - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [23 Jan - 25 Jan](https://www.expedia.co.uk/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) In three months [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [20 Mar - 22 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in South Side ![Interior](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-aea79261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-0f9df4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/de537c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/104000000/103330000/103320500/103320435/w1349h899x1y1-c30de37e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Brighton Park 10/10 Exceptional (1) "Family-friendly, quiet, perfect for a family or friends vacationing in Chicago. The apartment is very clean and the host was always available and responded quickly. The next time I come to Chicago, i will definitely stay at the apartment \[if available\]. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fabian H. [](https://www.expedia.co.uk/Chicago-Hotels-Spacious-3-Bedroom-Apartment-10-Minutes-To-Downtown-Sleeps-Up-To-10.h103320435.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-e0042c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1349h899x1y1-922f1c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-24e41c53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/97000000/96480000/96479300/96479287/w1350h899x0y1-7f0cda99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Brighton Park 9.2/10 Wonderful (7) "It was great it had the basic amenities for a family to enjoy the stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damary T. £201 includes taxes & fees 8 Dec - 9 Dec [](https://www.expedia.co.uk/Chicago-Hotels-W-Pershing-Large-Chicago-Apt-3-Bed-12-Min-Downtown-Arcade.h96479287.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/4815e87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/0d5faef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/554d2dcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/94f801a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park 10/10 Exceptional (1) "We had a great stay. Location is in nice neighborhood with walking access to restaurants and university of Chicago. Apartment was clean and as pictured. Would stay again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) christine m. £125 includes taxes & fees 3 Dec - 4 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Modern-1BR-Gem-In-Chicago-Kenwood-501.h116792457.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) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/0e90abd7.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) ![1 bedroom, travel cot, 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) ### Apartment in Hyde Park 9.0/10 Wonderful (6) "Our stay was very nice, with simple checkin / check out, and excellent communication by our host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom B. £125 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Chic-Retreat-Cozy-1BR-Apartment.h116792510.Hotel-Information) ![Iron/ironing board, travel cot, 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/117000000/116800000/116793100/116793083/829bcf7a.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/1a4d0483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park 9.4/10 Exceptional (9) "Clean room and convenient location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabriela £121 includes taxes & fees 7 Dec - 8 Dec [](https://www.expedia.co.uk/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) ![1 bedroom, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793062/a606f1f6.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) ![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) ### Apartment in Hyde Park 10/10 Exceptional (2) "This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan F. £125 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Bright-Cozy-1BR-Near-UChicago.h116793062.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/66917406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/eebdb633.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/ffe46ceb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/032eb104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park 10/10 Exceptional (2) "Location was just perfect!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meg D. £121 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Studio-Unit-Chic-Prime-Location.h116792582.Hotel-Information) ![Iron/ironing board, travel cot, 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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117130000/117124300/117124263/32c9cb69.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) ### Apartment in Hyde Park 10/10 Exceptional (1) £121 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Charm-Studio-Apt-In-Chicago.h117124263.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/c4821ce0.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/117000000/116240000/116238300/116238230/w1080h1353x0y0-3dea97aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/74d36cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116240000/116238300/116238230/w1080h1440x0y16-cbb4ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Calumet Park 10/10 Exceptional (5) "Lakeia was very accommodating throughout our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy K. £249 includes taxes & fees 2 Dec - 3 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Relax-Unwind-In-This-Comfortable-3BR-Unit.h116238230.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/8682a3d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/269d384b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/8f43eb0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792423/235673cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Greater Grand Crossing 10/10 Exceptional (2) "Very happy with stay. Good communication from property host. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole E. £239 includes taxes & fees 25 Nov - 26 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Stylish-4BR-South-Loop-Home.h116792423.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/3ded30c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/7d0f8c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/7e43465a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/f6353a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park 9.6/10 Exceptional (4) "Nice place for a girls trip weekend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madonna A. £142 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Sleek-Functional-2-Bedroom-Apt.h116792489.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793049/725729b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793049/41851f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793049/0aa9ff95.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/117000000/116800000/116793100/116793049/eb91a024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park 10/10 Exceptional (2) "My stay was really good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paramita B. £125 includes taxes & fees 2 Dec - 3 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Studio-Apt-Comfy-Sunlit.h116793049.Hotel-Information) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/49b10dc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/80d49650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/0327bf8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792497/02fd94e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park 9.6/10 Exceptional (4) "Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin W. £151 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Furnished-3BR-Apt-W-Laundry.h116792497.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/bc32b3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/7608b471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/7a89868d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/113000000/112540000/112534100/112534056/59cc12db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Bronzeville 10/10 Exceptional (3) "What a great place to stay! Interior of the unit was very nice and modern. Amenities were great. We felt safe and secure the entire time. Our host was in constant communication to make sure our needs were met. We would definitely recommend this stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matt D. £235 includes taxes & fees 25 Nov - 26 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Spacious-Stay-In-Historic-Bronzeville.h112534056.Hotel-Information) ![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/e861b994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/0c6cc9cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/d815691e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792479/ae8fd0e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park 10/10 Exceptional (1) "Great place to stay. It was easy to settle in and relax after a long day of traveling. The bed was comfortable and great to sleep on. Will definitely try for this property again if I need to come to the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael S. £125 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Bright-Modern-1BR-In-Hyde-Park.h116792479.Hotel-Information) ![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) ![Classic Apartment | Private kitchen](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/d0a14058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment | Free WiFi](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/w2571h1446x1y1-ccdca671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aparthotel in Bridgeport £296 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Stylish-Apartment-Near-Chicago-Downtown.h119973593.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/c283a70a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/dfaa443f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/d2647f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/9f09ad08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park 6.8/10 (3) "Very nice place! Not many kitchen amenities available as there was no way to heat up something in the oven with no baking sheet or foil. Getting into the apartment was not very easy as we had to call a number to be remotely let in every time we wanted to use the front door." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teri D. £151 includes taxes & fees 25 Nov - 26 Nov [](https://www.expedia.co.uk/Chicago-Hotels-3BR-Complete-Well-Located.h116792567.Hotel-Information) ![WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792451/24fa79a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, toaster](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792451/52d9308c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, toaster](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792451/c67dc51a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792451/2bf9ca15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park £121 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Trendy-Studio-In-Vibrant-Area.h116792451.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/99e40178.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/ab2a4e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/900036cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792541/279f144b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Hyde Park £121 includes taxes & fees 3 Dec - 4 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Compact-Studio-For-A-Relaxed-Stay.h116792541.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/120000000/119470000/119468300/119468277/2e29ddad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/120000000/119470000/119468300/119468277/b7f4ff98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119470000/119468300/119468277/1389f1f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel cot, bed sheets](https://images.trvl-media.com/lodging/120000000/119470000/119468300/119468277/556fb412.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment in Kenwood 8.0/10 Very good (2) "This was lovely! I stayed due to closeness to my wedding ceremony location and wanted somewhere to get ready. The apartment was DARLING (it's so spacious!) and had everything I needed. The bed was very comfortable. Host was professional and polite and very helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jade R. £125 includes taxes & fees 3 Dec - 4 Dec [](https://www.expedia.co.uk/Chicago-Hotels-Homey-Vibes-Furnished-1BR-Apt.h119468277.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.co.uk/Hotel-Search?startDate=2025-12-08&endDate=2025-12-09®ionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=VR_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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals) ## Top South Side Hotel Reviews ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Great experience" [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.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 "Nice" [](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.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 "the room was spotless, and it was quiet. " [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg) ### Sophy Hyde Park 10/10 Excellent "Room and location were great" [](https://expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.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.co.uk/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.co.uk/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.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 "The room was spotless and check in staff was courteous. " [](https://expedia.co.uk/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![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 room, staff, and facilities were amazing, even breakfast was delicious!" [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.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 "The staff were friendly and helpful. The room was very clean. Breakfast was good. " [](https://expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ## Find out more about South Side **Everything you need to know about** **South Side** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Side holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **South Side holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Side holiday rentals we have selected for you start as low as £121 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 holiday 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 holiday. 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.co.uk - All accommodation types in South Side ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - 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