Title: Best South Side Condo Rental in 2026 | 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)[Holiday Rentals in South Side](https://expedia.co.uk/South-Side-Holiday-Rentals.d553248635074842823.Travel-Guide-HolidayRentals)[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 South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__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 [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 two months [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side condo rentals ![TV](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/3c86e3c5.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) ![Exterior](https://images.trvl-media.com/lodging/104000000/103280000/103277000/103276998/657afb11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Comfortable Condo in the Heart of Bronzeville by RedAwning [](https://www.expedia.co.uk/Chicago-Hotels-Comfortable-Condo-In-The-Heart-Of-Bronzeville-By-RedAwning.h103276998.Hotel-Information) Bronzeville 7.8/10 Good (6 reviews) "Very clean, everything needed with in. Manager was easily accessible. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosheena C. £306 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Comfortable-Condo-In-The-Heart-Of-Bronzeville-By-RedAwning.h103276998.Hotel-Information) ![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/2146175e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/21d3545d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/7716e8c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/a067dc99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Urban Retreat Near Wrigley Field w/Parking [](https://www.expedia.co.uk/Chicago-Hotels-Chic-Urban-Retreat-Near-Wrigley-Field-WParking.h100783919.Hotel-Information) Lakeview 10/10 Exceptional (46 reviews) "Great spot in a wonderful location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jasson R. £279 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Chic-Urban-Retreat-Near-Wrigley-Field-WParking.h100783919.Hotel-Information) ![Beach nearby, beach towels](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/0226147a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/4463d78c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/583d104b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99550000/99542100/99542070/92dc4cf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serenity on the Shores - with easy transport to Chicago/SouthShore across the St [](https://www.expedia.co.uk/Portage-Hotels-Serenity-On-The-Shores-With-Easy-Transport-To-ChicagoSouthShore-Across-The-St.h99542070.Hotel-Information) Portage 9.6/10 Exceptional (12 reviews) "Very nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LeAnna M. £168 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Portage-Hotels-Serenity-On-The-Shores-With-Easy-Transport-To-ChicagoSouthShore-Across-The-St.h99542070.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/f8b770f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/ef7d4602.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/w3000h1869x0y131-9607ee5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/84000000/83580000/83571000/83570994/8b428166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Suite/Mins to L Train /Laundry/Free Parking [](https://www.expedia.co.uk/Chicago-Hotels-Chic-SuiteMins-To-L-Train-LaundryFree-Parking.h83570994.Hotel-Information) Oak Park 9.6/10 Exceptional (58 reviews) "Super convenient if you want to see the Frank Lloyd wright house - walked to studio and train and great cafes. Perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Travis S. £158 includes taxes & fees 7 Mar - 8 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Chic-SuiteMins-To-L-Train-LaundryFree-Parking.h83570994.Hotel-Information) ![Paper towels](https://images.trvl-media.com/lodging/91000000/90900000/90893200/90893149/w1024h677x0y3-d728bf96.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/91000000/90900000/90893200/90893149/w1024h677x0y3-8b061d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90900000/90893200/90893149/w1024h678x0y3-13685302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/91000000/90900000/90893200/90893149/w1024h678x0y3-3dec758e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Just remodeled apartment close to airport and mall [](https://www.expedia.co.uk/Chicago-Hotels-Just-Remodeled-Apartment-Close-To-Airport-And-Mall.h90893149.Hotel-Information) Elk Grove Village 10/10 Exceptional (15 reviews) "Very nice place to stay in secure neighborhood " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina F. £190 includes taxes & fees 11 Feb - 12 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Just-Remodeled-Apartment-Close-To-Airport-And-Mall.h90893149.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/ce65ca8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/73c43643.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/b0d35ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/54265791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Air-Conditioned King Suite | Complimentary Breakfast [](https://www.expedia.co.uk/Chicago-Hotels-Air-Conditioned-King-Suite-Complimentary-Breakfast.h115327535.Hotel-Information) York Center 9.0/10 Wonderful (2 reviews) "Very nice facility. Room was spacious and comfortable. Staff were friendly and helpful. Had a great experience. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffery R. £120 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Air-Conditioned-King-Suite-Complimentary-Breakfast.h115327535.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/124000000/123190000/123181700/123181684/2535800a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123190000/123181700/123181684/8825b812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/124000000/123190000/123181700/123181684/4594e979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel cot, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123190000/123181700/123181684/a9b32b45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 2-Bedroom Condo – Easy Drive to Downtown Chicago & Midway Airport [](https://www.expedia.co.uk/Chicago-Hotels-Stylish-2-Bedroom-Condo-Easy-Drive-To-Downtown-Chicago-Midway-Airport.h123181684.Hotel-Information) Stickney 9.0/10 Wonderful (2 reviews) "100% recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ana Maria I. £233 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Stylish-2-Bedroom-Condo-Easy-Drive-To-Downtown-Chicago-Midway-Airport.h123181684.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/83000000/83000000/83000000/82999916/d99ed1e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/83000000/83000000/83000000/82999916/71f507ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/83000000/83000000/82999916/28334f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/83000000/83000000/83000000/82999916/15ebf54b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Free Breakfast. Indoor Pool. Gym. Business Center. [](https://www.expedia.co.uk/Schererville-Hotels-Free-Breakfast-Indoor-Pool-Gym-Business-Center.h82999916.Hotel-Information) Schererville £175 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Schererville-Hotels-Free-Breakfast-Indoor-Pool-Gym-Business-Center.h82999916.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/d68966c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/f0e190e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/9796e9bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/e9c1d662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field MVP Suite 1 Bedroom Apartment [](https://www.expedia.co.uk/Chicago-Hotels-Wrigleyville-Inn.h34913312.Hotel-Information) Lakeview 9.6/10 Exceptional (14 reviews) "Great location. 30 steps to Wrigley field. Clean. Safe. Very clean apt." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Curt M. £491 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Wrigleyville-Inn.h34913312.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/65000000/64620000/64617800/64617797/w917h683x54y0-2119987a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/65000000/64620000/64617800/64617797/5502dc92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64620000/64617800/64617797/w917h683x48y0-6ac49149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/65000000/64620000/64617800/64617797/150d1105.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy One Bedroom, Washer Dryer, Central Location, Fireplace, Monthly Discounts [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-One-Bedroom.h64617797.Hotel-Information) Lombard 9.2/10 Wonderful (22 reviews) "Good location, clean, and very well kept" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David A. £259 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-One-Bedroom.h64617797.Hotel-Information) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/91000000/90130000/90125900/90125808/1504e9cc.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/91000000/90130000/90125900/90125808/c72de563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, printers](https://images.trvl-media.com/lodging/91000000/90130000/90125900/90125808/7dd36329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90130000/90125900/90125808/e6a70047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking [](https://www.expedia.co.uk/Chicago-Hotels-MDRN-Kid-Friendly-AptCharmingPrivateSunnyFast-Wi-Fi-Parking.h90125808.Hotel-Information) South Evanston 9.6/10 Exceptional (25 reviews) "Good place to stay, comfortable and quiet." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew N. £459 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-MDRN-Kid-Friendly-AptCharmingPrivateSunnyFast-Wi-Fi-Parking.h90125808.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/cb1524af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/2c42d6c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/881a5b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/5f4153b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field All Star Suite 3 Bedrooms 2 Bath [](https://www.expedia.co.uk/Chicago-Hotels-Wrigleyville-Inn-AllStar-Unit.h33962122.Hotel-Information) Lakeview 9.4/10 Exceptional (22 reviews) "Everything was excellent. Highly recommended!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald S. £694 includes taxes & fees 7 Feb - 8 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Wrigleyville-Inn-AllStar-Unit.h33962122.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/40eab497.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/9e1f9bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/b749cf49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/315f6012.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fully-Equipped Suite | Gym Access [](https://www.expedia.co.uk/Chicago-Hotels-Fully-Equipped-Suite-Gym-Access.h115327527.Hotel-Information) York Center £118 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Fully-Equipped-Suite-Gym-Access.h115327527.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/db5aefbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory-foam beds](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/w1055h795x5y0-32f5e83c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory-foam beds](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/66d4fb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/59f4093c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Home Run 4 Bedroom, 2 Bathroom [](https://www.expedia.co.uk/Chicago-Hotels-Gorgeous-4-Bedroom-With-Pool-Table-Steps-From-Wrigley-Field-Sleeps-9.h34821849.Hotel-Information) Lakeview 9.6/10 Exceptional (20 reviews) "Would definitely stay there again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Enrique £801 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Gorgeous-4-Bedroom-With-Pool-Table-Steps-From-Wrigley-Field-Sleeps-9.h34821849.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/4af11984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/b63f36bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/d26c07a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/8b5408c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bedroom | Free Daily Breakfast. Indoor Pool. [](https://www.expedia.co.uk/Schererville-Hotels-2-Bedroom-Free-Daily-Breakfast-Indoor-Pool.h88274464.Hotel-Information) Schererville £277 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Schererville-Hotels-2-Bedroom-Free-Daily-Breakfast-Indoor-Pool.h88274464.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/b3be6fd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/b4610d8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/5099ab10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/c59160d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed Suite | Indoor Pool. Free Breakfast. [](https://www.expedia.co.uk/Schererville-Hotels-King-Bed-Suite-Indoor-Pool-Free-Breakfast.h86147480.Hotel-Information) Schererville £297 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Schererville-Hotels-King-Bed-Suite-Indoor-Pool-Free-Breakfast.h86147480.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/93c5f874.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/e54a5b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/8db3e70f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/d815e728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom [](https://www.expedia.co.uk/Chicago-Hotels-The-Inn-At-Wrigleyville.h33912904.Hotel-Information) Lakeview 10/10 Exceptional (22 reviews) "Place is freaking perfect if you're in town for some sight seeing and a ball game." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elbert C. £801 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Chicago-Hotels-The-Inn-At-Wrigleyville.h33912904.Hotel-Information) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/79e701e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory-foam beds](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/w1055h795x5y0-30a82df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/15eb4dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/931c944e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms [](https://www.expedia.co.uk/Chicago-Hotels-Across-From-Wrigley-Field.h34002204.Hotel-Information) Lakeview 9.6/10 Exceptional (28 reviews) "The location was amazing! Comfortable beds and easy access. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald N. £801 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Across-From-Wrigley-Field.h34002204.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/3c71ed9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory-foam beds](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/81bc10e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/73f8ab11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, memory-foam beds](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/d3d80bf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms [](https://www.expedia.co.uk/Chicago-Hotels-Featured-On-The-Travel-Channel.h35179280.Hotel-Information) Lakeview 9.0/10 Wonderful (15 reviews) "The apartment is literally across the street from the ballpark. Very clean, easy to check in, big space, everything we needed was there, couldn't have asked for more." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) vince h. £801 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Featured-On-The-Travel-Channel.h35179280.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/548e9e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/b9fff8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/1608199a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/1ebbfb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fully-Equipped Suite | Complimentary Breakfast [](https://www.expedia.co.uk/Chicago-Hotels-Fully-Equipped-Suite-Complimentary-Breakfast.h85478628.Hotel-Information) York Center 2.0/10 (1 review) "Hotel staff were great. “Suite” was a total disaster. Carpets were at least 10 years old with holes and furniture was as old and very uncomfortable. Never would have rented this “Suite” if we knew the true condition. Online pictures paint a very different picture." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul S. £110 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Fully-Equipped-Suite-Complimentary-Breakfast.h85478628.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=2026-02-20&endDate=2026-02-21®ionId=553248635074842823&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=APARTMENT) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VILLA) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=CONDO) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=COTTAGE) Residences [](https://www.expedia.co.uk/Hotel-Search?destination=South+Side%2C+Illinois%2C+United+States+of+America®ionId=553248635074842823&latLong=41.805466%2C-87.608765&adults=2&startDate=2026-05-07&d1=2026-05-07&endDate=2026-05-10&d2=2026-05-10&lodging=RESIDENCE) ![](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-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouth-Side-Condos.d553248635074842823-aaCondos.Travel-Guide-Accommodation) ## Top South Side Hotel Reviews ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg) ### Holiday Inn Chicago – Midway Airport S by IHG 10/10 Excellent "Staff very friendly " [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.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 "Loved it " [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Great rooms With upgraded, Recently Renovated! " [](https://expedia.co.uk/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.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 "Friendly staff, clean room, quiet. " [](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 "All great!" [](https://expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.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 "Good stay" [](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Great service and clean roomd" [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7_y.jpg) ### Sophy Hyde Park 10/10 Excellent "This is the prettiest hotel I have ever visited. Beautiful artwork throughout a very modern, clean, and friendly place. I most definitely will return!" [](https://expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![ LakeHouse](https://images.trvl-media.com/lodging/71000000/70890000/70886100/70886010/03d3c9c4_y.jpg) ### LakeHouse 10/10 Excellent "Enjoyed the space for a staycation, the host was very responsive in troubleshooting a booking issue. Loved the rooftop and balcony access " [](https://expedia.co.uk/Chicago-Hotels-LakeHouse.h70886010.Hotel-Information) ## Find out more about South Side ## South Side Condo Rentals information | Number of reviews | 268 | | ----------------- | ---------------- | | Accommodation | 45 Condo Rentals | | Lowest Price | £110 | | Highest Price | £801 | ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - More ways to book - [4 Star Hotels in McKinley Park ](https://www.expedia.co.uk/4Star-McKinley-Park-Chicago-Hotels.s40-n6132389-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in New City ](https://www.expedia.co.uk/5Star-New-City-Chicago-Hotels.s50-n6132388-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Armour Square ](https://www.expedia.co.uk/Armour-Square-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132365-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Bridgeport Hotels ](https://www.expedia.co.uk/Bridgeport-Chicago-Hotels.0-n6132075-0.Travel-Guide-Filter-Hotels) - 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