Title: Holiday Rentals South Side from £135: 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) ![](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 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 [24 Oct - 26 Oct](https://www.expedia.co.uk/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) In one month [7 Nov - 9 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [2 Jan - 4 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-01-02&endDate=2026-01-04&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 ![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 | 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) ![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/120000000/119980000/119973600/119973593/58a3b7eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Apartment near Chicago Downtown Bridgeport £255 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/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 cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/77ca5eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792603/873e46ea.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 (6) "This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. " £135 includes taxes & fees 15 Oct - 16 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Studio-In-Hyde-Park-Walk-To-Lake-University.h116792603.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) ![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) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/d10b773f.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) ### Modern Studio Near UChicago Hyde Park 10/10 Exceptional (6) £135 includes taxes & fees 15 Oct - 16 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Studio-Near-UChicago.h116793083.Hotel-Information) ![1 bedroom, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/de22ad61.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) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/b97e6643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793085/3c0301b3.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!" £143 includes taxes & fees 21 Oct - 22 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Modern-1BR-In-Historic-HydePark.h116793085.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) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792510/f2aa28b0.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 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) ### 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. " £143 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Chic-Retreat-Cozy-1BR-Apartment.h116792510.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) ![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) ![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) ### 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.co.uk/Chicago-Hotels-A-Home-Away-From-Home.h103943206.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) ![Interior](https://images.trvl-media.com/lodging/95000000/94730000/94721400/94721307/e1e23183.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 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.co.uk/Chicago-Hotels-Elegant-Mayors-Manor-In-Central-Chicago-9-Beds.h94721307.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111920000/111920000/111919926/c250c305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111920000/111920000/111919926/2552de3e.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/112000000/111920000/111920000/111919926/048915f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111920000/111920000/111919926/0875a7ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Animal House Near Sox Stadium Bridgeport 8.0/10 Very good (11) "It was very cute! I enjoyed staying here" [](https://www.expedia.co.uk/Chicago-Hotels-Animal-House-Near-Sox-Stadium.h111919926.Hotel-Information) ![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/b84b9af4.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) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792638/29086b5a.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." £169 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Bright-Spacious-2BR-Prime-Hyde-Park-Location.h116792638.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/03d3c9c4.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/71000000/70890000/70886100/70886010/a351b4ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/w828h549x0y0-b2df28f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/554617f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LakeHouse South Shore 9.4/10 Exceptional (21) "Everything was perfect with the property and the host even came to help right away when we had one issue with the lights." [](https://www.expedia.co.uk/Chicago-Hotels-LakeHouse.h70886010.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/b96a4021.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 7.4/10 Good (3) "The house was absolutely beautiful ! Very spacious and nice! Comfy beds and clean. " [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Duplex-Obama-University-Chicago-Area-3BR.h105642745.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/48f8f2b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/4fff30c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/c5e0d032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792556/2a25922f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Explore Hyde Park: 2BR Apt on Blackstone Ave Hyde Park £177 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Explore-Hyde-Park-2BR-Apt-On-Blackstone-Ave.h116792556.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) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/5349db93.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.co.uk/Chicago-Hotels-Comfortable-Condo-In-The-Heart-Of-Bronzeville-By-RedAwning.h103276998.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) ![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) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792567/dfaa443f.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) ### 3BR | Complete & Well-Located 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." £219 includes taxes & fees 15 Oct - 16 Oct [](https://www.expedia.co.uk/Chicago-Hotels-3BR-Complete-Well-Located.h116792567.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/105000000/104350000/104341900/104341807/531c4a08.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.co.uk/Chicago-Hotels-Modern-Condo-Obama-University-Of-Chicago-Area.h104341807.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/w905h683x60y0-9699e2f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/w904h683x60y0-a23ee43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/w904h683x60y0-c5e62d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83100000/83093200/83093121/w905h683x60y0-4afddd3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheerful 4 bedroom smart home w/ indoor fireplace Washington Park 7.8/10 Good (18) "The property is shown accurately in the photos. It was pretty clean. Its centrally located to eateries and shopping. Need more pillows, had no window coverings and had to contact tbe host for the correct code to the door.Would stay again." [](https://www.expedia.co.uk/Chicago-Hotels-Cheerful-4-Bedroom-Smart-Home-W-Indoor-Fireplace.h83093121.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/93000000/92090000/92082100/92082063/e0a97b58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/93000000/92090000/92082100/92082063/eb4699ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92090000/92082100/92082063/4777f6c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, shampoo, toilet paper](https://images.trvl-media.com/lodging/93000000/92090000/92082100/92082063/b7f534b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely 3-bedroom apartment in Bronzeville Bronzeville 9.6/10 Exceptional (32) "The House is nice and is located in a beutiful and peaceful area." [](https://www.expedia.co.uk/Chicago-Hotels-Lovely-3-Bedroom-Apartment-In-Bronzeville.h92082063.Hotel-Information) ![Iron/ironing board, travel cot, 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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792600/116792582/da920a3a.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) ### Cozy Studio in Chicago Hyde Park £136 includes taxes & fees 20 Oct - 21 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-Studio-In-Chicago.h116792582.Hotel-Information) ![Iron/ironing board, travel cot, 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) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792700/116792613/0b1f4ad5.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/117000000/116800000/116792700/116792613/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) ### Trendy Studio Apartment in Chicago Hyde Park £148 includes taxes & fees 21 Oct - 22 Oct [](https://www.expedia.co.uk/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) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119430000/119426700/119426636/c7942c29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay, Relax & Explore Chicago Greater Grand Crossing 8.0/10 Very good (1) "Very nice property!" [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2025-10-24&endDate=2025-10-25®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.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 ![Mccormick Place Guest House](//images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/b6c2dad6_y.jpg) ### Mccormick Place Guest House 10/10 Excellent "Awesome and unique decor! " [](https://expedia.co.uk/Chicago-Hotels-Mccormick-Place-Guest-House.h22670906.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.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.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 "Safe area good staff " [](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![SpringHill Suites by Marriott Chicago Chinatown](//images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg) ### SpringHill Suites by Marriott Chicago Chinatown 10/10 Excellent "Variety of good restaurants around. Great service " [](https://expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.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.co.uk/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.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.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 "The room was clean and cute. It had a comfortable bed and a desk and that’s all we really needed. The area was fairly quiet and a great location to catch a bus or take a quick drive to the parts of city we visited (The Loop and Hyde Park). We had access to street parking directly in front of the property. The shared common areas were a fun aesthetic and very tidy. Online communication with the property managers was timely and direct. We definitely enjoyed our brief stay :)" [](https://expedia.co.uk/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Chinatown Hotel Chicago](//images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Lots of affordable parking in the area and right by the red line" [](https://expedia.co.uk/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.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.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.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 £135 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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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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)