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 [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [17 Jul - 19 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-07-17&endDate=2026-07-19&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 ![Interior](https://images.trvl-media.com/lodging/116000000/115060000/115059100/115059038/cd46c40d.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/116000000/115060000/115059100/115059038/d77efe88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/116000000/115060000/115059100/115059038/92350f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/116000000/115060000/115059100/115059038/948fbc9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ModernFarmHouseChicago-Spacious 3-bedroom condo Near Downtown Chicago [](https://www.expedia.co.uk/Chicago-Hotels-ModernFarmHouseChicago-Spacious-3-Bedroom-Condo-Near-Downtown-Chicago.h115059038.Hotel-Information) Kenwood £353 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Chicago-Hotels-ModernFarmHouseChicago-Spacious-3-Bedroom-Condo-Near-Downtown-Chicago.h115059038.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) ![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) ![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) ### 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 (60 reviews) "Comfortable bed, spacious rooms and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael W. £160 includes taxes & fees 25 Mar - 26 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) ![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) ![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) ![Pool](https://images.trvl-media.com/lodging/91000000/90900000/90893200/90893149/w1024h677x0y3-a16fc2a7.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 (16 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 6 Apr - 7 Apr [](https://www.expedia.co.uk/Chicago-Hotels-Just-Remodeled-Apartment-Close-To-Airport-And-Mall.h90893149.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) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90130000/90125900/90125808/e6a70047.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) ![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) ### 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 (26 reviews) "The apartment is warm and cozy, plenty of space. The host was very responsive throughout. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vernon S. £347 includes taxes & fees 26 Mar - 27 Mar [](https://www.expedia.co.uk/Chicago-Hotels-MDRN-Kid-Friendly-AptCharmingPrivateSunnyFast-Wi-Fi-Parking.h90125808.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/w544h683x240y0-345df6c1.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) ![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) ### 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. £260 includes taxes & fees 25 Mar - 26 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-One-Bedroom.h64617797.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) ![Exterior detail](https://images.trvl-media.com/lodging/101000000/100790000/100784000/100783919/a067dc99.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) ### 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 (49 reviews) "Great spot in a wonderful location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jasson R. £280 includes taxes & fees 13 Apr - 14 Apr [](https://www.expedia.co.uk/Chicago-Hotels-Chic-Urban-Retreat-Near-Wrigley-Field-WParking.h100783919.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) ![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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123190000/123181700/123181684/45796b12.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. £212 includes taxes & fees 20 Apr - 21 Apr [](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/89000000/88280000/88274500/88274464/4af11984.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) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/89000000/88280000/88274500/88274464/e2fa30cc.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) ### 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 £318 includes taxes & fees 23 Apr - 24 Apr [](https://www.expedia.co.uk/Schererville-Hotels-2-Bedroom-Free-Daily-Breakfast-Indoor-Pool.h88274464.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327527/9e1f9bd9.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 £128 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Fully-Equipped-Suite-Gym-Access.h115327527.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) ![Bathroom](https://images.trvl-media.com/lodging/35000000/34920000/34913400/34913312/e9c1d662.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) ### 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. £496 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Chicago-Hotels-Wrigleyville-Inn.h34913312.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) ![Hair dryer, towels](https://images.trvl-media.com/lodging/34000000/33970000/33962200/33962122/e19d134a.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) ![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) ### 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. £705 includes taxes & fees 27 Mar - 28 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Wrigleyville-Inn-AllStar-Unit.h33962122.Hotel-Information) ![Smart TV, fireplace, video game console, books](https://images.trvl-media.com/lodging/74000000/73570000/73569200/73569123/88c4d702.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/74000000/73570000/73569200/73569123/5d3d56c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video game console, books](https://images.trvl-media.com/lodging/74000000/73570000/73569200/73569123/cfdd6907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73570000/73569200/73569123/w1280h872x0y31-19c53dad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Chicago 3BR/3BA • Sleeps 7 • Near Downtown [](https://www.expedia.co.uk/Chicago-Hotels-Large-Chicago-3BR3BA-Sleeps-7-Near-Downtown.h73569123.Hotel-Information) West Town 10/10 Exceptional (34 reviews) "Stayed here for a weekend to explore Chicago and this place was perfect. House was clean, well kept and has a great layout. The location is also perfect for exploring the greater Chicago area. Would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew L. £647 includes taxes & fees 4 Apr - 5 Apr [](https://www.expedia.co.uk/Chicago-Hotels-Large-Chicago-3BR3BA-Sleeps-7-Near-Downtown.h73569123.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/35000000/34830000/34821900/34821849/66d4fb68.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) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34830000/34821900/34821849/57dfa3ee.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 £804 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Chicago-Hotels-Gorgeous-4-Bedroom-With-Pool-Table-Steps-From-Wrigley-Field-Sleeps-9.h34821849.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) ![Lobby](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/54265791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115330000/115327600/115327535/0b6ef485.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) ### 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. £127 includes taxes & fees 29 Mar - 30 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Air-Conditioned-King-Suite-Complimentary-Breakfast.h115327535.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) ![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) ![Interior](https://images.trvl-media.com/lodging/87000000/86150000/86147500/86147480/140f544e.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 8.0/10 Very good (1 review) £339 includes taxes & fees 12 Apr - 13 Apr [](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) ![4 bedrooms](https://images.trvl-media.com/lodging/34000000/33920000/33913000/33912904/w1055h795x5y0-8aae4c37.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. £804 includes taxes & fees 6 Apr - 7 Apr [](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) ![Fireplace](https://images.trvl-media.com/lodging/35000000/34010000/34002300/34002204/931c944e.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) ### 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 (29 reviews) "Host was great! Let us check in early, it was an easy check in/out! We'll be back for a Cubs game! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline B. £804 includes taxes & fees 6 Apr - 7 Apr [](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) ![Living area](https://images.trvl-media.com/lodging/36000000/35180000/35179300/35179280/a0078d7b.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. £809 includes taxes & fees 27 Mar - 28 Mar [](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) ![Dining](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/1ebbfb68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/86000000/85480000/85478700/85478628/15424f94.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. £127 includes taxes & fees 5 Apr - 6 Apr [](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=2026-04-07&endDate=2026-04-08®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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VILLA) Cabins [](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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CABIN) 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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=COTTAGE) 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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VACATION_HOME) ![](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 ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/efb1181a_y.jpg) ### Carlton Inn Midway 4/10 Poor "El cuarto olía mucho a cigarro y según era no fumar. " [](https://expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Had a great stay " [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg) ### Holiday Inn Chicago – Midway Airport S by IHG 10/10 Excellent "Great staff , enjoyed our stay , very close to where we needed to be " [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/099e5443_y.jpg) ### Chinatown Hotel Chicago 2/10 Terrible "This was hands down the worst hotel I've ever seen. Mattress was covered in piss stains, there was puke on the computer desk, the blinds were broken, dresser was missing drawers, the bad frame was straight up made of 2x4's, and the dude at the front desk was on a personal call the entire time he was checking me in. They also offer you a free can of Coke if you give them a 10/10 review. So desperate. I'm trying to get a refund right now because we refused to stay there under such conditions. STAY AWAY FROM THIS PLACE. " [](https://expedia.co.uk/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!](https://images.trvl-media.com/lodging/74000000/73640000/73639200/73639173/e6f80b77_y.jpg) ### Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! 8/10 Good "Lack of amenities " [](https://expedia.co.uk/Chicago-Hotels-Comfy-4-Bedroom-Apartment-In-The-Center-Of-CHICAGO-15-Mins-From-Downtown.h73639173.Hotel-Information) ![Sophy Hyde Park](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f1fd01e1_y.jpg) ### Sophy Hyde Park 10/10 Excellent "This is my Chicago home away from home - it is beautiful " [](https://expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/e8f8e393_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 8/10 Good "Bathroom extremely clean " [](https://expedia.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Chicago Lake Shore Hotel](https://images.trvl-media.com/lodging/1000000/10000/7400/7341/5dc5b9fc_y.jpg) ### Chicago Lake Shore Hotel 8/10 Good "The room was really spotless. Really comfortable bed and the pillows are nice as well. Comes with microwave and fridge as well. However the shower head pressure was significantly weak. And the plugs for both nightstands didn't work. It would have been nice if there were a complimentary breakfast as well.But overall the room was really good. " [](https://expedia.co.uk/Chicago-Hotels-Chicago-Lake-Shore-Hotel.h7341.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 "CLEAN room. Respectable staff. Good location near McCormick Place Convention Center. Would definitely stay again! Thank you!" [](https://expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ## Find out more about South Side ## South Side Condo Rentals information | Number of reviews | 334 | | ----------------- | ---------------- | | Accommodation | 45 Condo Rentals | | Lowest Price | £127 | | Highest Price | £809 | ## 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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