Title: The 10 Best 2 Star Hotels in South Side - 2025 Updated Prices | 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) ![](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) # Compare and book 2 Star hotels in South Side, Chicago ### Change your mind Book hotels with free cancellation ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ### Be picky Search almost a million properties worldwide ## Check availability on South Side 2 Star Hotels Tonight [7 Oct - 8 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-07&endDate=2025-10-08&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [8 Oct - 9 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-08&endDate=2025-10-09&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [10 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side 2 Star Hotels ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | In-room safe, desk, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/f80081f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/e8f8e393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/98e3ca35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG Bedford Park 9.0/10 Wonderful (1139) "nice spacious clean rooms - several restraunts / fast food / stores nearby" £100 includes taxes & fees 6 Nov - 7 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/626e0b20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/af2ab071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/5a8bb237.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 - Chicago, IL Washington Heights 6.6/10 (124) "Safe area good staff " £59 includes taxes & fees 21 Oct - 22 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Coffee and/or coffee maker](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/073ee6bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/26ad2ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/acd4cf26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carlton Inn Midway Archer Heights 6.4/10 (1004) "Front Desk attention was great." £104 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/62703e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bed sheets](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/093eee5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/10d8c32c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, towels](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/130fbf4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capital O Empire Motel Chicago I-94 Greater Grand Crossing 3.8/10 (18) "I would feel safer sleeping on the street than this motel. " £56 includes taxes & fees 9 Oct - 10 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Empire-Motel.h118831367.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/f5aef82f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking | Desk, blackout curtains, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/09cd06f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/ff20a621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Inn & Suites - Midway Airport Burbank 6.6/10 (1001) "Pleasant stuff, comfy bed, would stay again." £93 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Living room](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/e921e6b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/273b53b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chic 3 BR CONDO | Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d323a9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House Bronzeville 8.4/10 Very good (71) "Very convenient for a short term stay with private area and clean shared spaces the parking is very convenient as well" £70 includes taxes & fees 9 Oct - 10 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Hallway](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/19cdbb10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Smoking | 1 bedroom, desk, bed sheets](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/eaa24bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/f16d7e14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/7076eeb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Motel By OYO Chicago I-90 Woodlawn 3.4/10 (45) "Easy, safe parking " £80 includes taxes & fees 8 Oct - 9 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b66dd193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/d4687c67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b1d231c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, towels](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/026f1c9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Admiral Motel By Oyo Chicago I-94 Chatham 4.0/10 (33) "It was a great hotel" £61 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/84aefbd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/3da50eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini fridge](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/b118c2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/38fe6f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skylark Motel Garfield Ridge 4.6/10 (118) "Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal." £87 includes taxes & fees 12 Oct - 13 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/93b80b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/dccf4817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/e45ee1e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/b8a7cbaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rainbow Motel Garfield Ridge 5.8/10 (12) "It was a good stay the rooms are small tho but if you are going to have fun and just have somewhere to sleep then it’s perfect for a couple people " £80 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information) ![Microwave](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/16ff56fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/4e885a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/3eb04d9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/1050258f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago Bronzeville 9.8/10 Exceptional (13) "Served us well for our event near the McCormick Center. Hospitality was second to none! " [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-1-Bedroom-Apartment-With-WiFi.h107094905.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3835h2161x6y0-831944db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-e49145be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Mobility Accessible (Accessible Tub) | Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/eae811db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Chicago – Midway Airport S by IHG West Lawn 8.4/10 Very good (1000) "Great stay" [](https://www.expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/229b6322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/ba671201.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/4ec44f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/1b1902af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Lake Shore Hotel Kenwood 10/10 Exceptional (1) "Clean room but in need of renovation " [](https://www.expedia.co.uk/Chicago-Hotels-Ramada-Inn-Lake-Shore.h69827000.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109330000/109326800/109326777/2a7621bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors, printers](https://images.trvl-media.com/lodging/110000000/109330000/109326800/109326777/d938a2f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109330000/109326800/109326777/11898c0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, computer monitors, printers](https://images.trvl-media.com/lodging/110000000/109330000/109326800/109326777/6093fe74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 3-bedroom apartment in awesome Chicago with AC, WiFi Washington Park [](https://www.expedia.co.uk/Chicago-Hotels-Spacious-3-Bedroom-Apartment-In-Awesome-Chicago-With-AC.h109326777.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106880000/106875400/106875382/34617f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/107000000/106880000/106875400/106875382/0b62c593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106880000/106875400/106875382/5760e0b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106880000/106875400/106875382/a69cdee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom apartment in awesome Chicago with WiFi, AC Gage Park [](https://www.expedia.co.uk/Chicago-Hotels-Charming-2-Bedroom-Apartment-In-Awesome-Chicago-With-WiFi.h106875382.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106550000/106543700/106543613/bbdfbce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106550000/106543700/106543613/7ce91cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106550000/106543700/106543613/3de306fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106550000/106543700/106543613/15afa085.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Landmark; a comfy suite near McCormick Place Bronzeville 10/10 Exceptional (5) "A lovely place to rest after busy days in Chicago! Quiet and clean with all that is needed to catch-up with yourself." [](https://www.expedia.co.uk/Chicago-Hotels-The-Landmark-A-Comfy-Suite-Near-McCormick-Place.h106543613.Hotel-Information) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109370000/109364400/109364310/7d79d730.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109370000/109364400/109364310/e167cf45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109370000/109364400/109364310/59a746ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/110000000/109370000/109364400/109364310/301ea0bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3-bedroom condo near University of Chicago Woodlawn 10/10 Exceptional (1) "Property was nice and clean. Had everything we needed. About 20 mins to most places we wanted to go and very close to MSI. We had a great stay. " [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-3-Bedroom-Condo-Near-University-Of-Chicago.h109364310.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/defd0847.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/b96a4021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/a43ffef3.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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/109000000/108430000/108420500/108420492/f48a80a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108430000/108420500/108420492/013704e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108430000/108420500/108420492/d26d0550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/109000000/108430000/108420500/108420492/90eb135d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 4BDR in Chicago / 15mins from DWTN Brand New! South Shore 10/10 Exceptional (3) "10/10 very clean very nice looks just like the pictures " [](https://www.expedia.co.uk/Chicago-Hotels-Gorgeous-4BDR-In-Chicago-15mins-From-DWTN-Brand-New.h108420492.Hotel-Information) ![Smart TV, fireplace, video games, table football](https://images.trvl-media.com/lodging/107000000/106770000/106765300/106765283/5f0dbb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106770000/106765300/106765283/60e9e92a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/107000000/106770000/106765300/106765283/f4efcf80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/107000000/106770000/106765300/106765283/65964f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games! Gresham 10/10 Exceptional (1) "Great lot of space " [](https://www.expedia.co.uk/Chicago-Hotels-Gorgeous-5-Bedroom-Gem-Sleeps-18-With-Pool.h106765283.Hotel-Information) ![](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%2F2Star-South-Side-Hotels.s20-0-d553248635074842823.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-South-Side-Hotels.s20-0-d553248635074842823.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in South Side. ![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Place Chicago-South/University Medical Center 5225 S Harper Ave, Chicago, IL £187 3 Nov - 4 Nov includes taxes & fees 8.6/10 Excellent! (1,017 reviews) [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### SpringHill Suites by Marriott Chicago Chinatown 2357 S WENTWORTH AVE, Chicago, IL £164 22 Oct - 23 Oct includes taxes & fees 9.4/10 Exceptional! (1,011 reviews) [](https://expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Jaslin Hotel 261 West Cermak Rd, Chicago, IL £127 30 Oct - 31 Oct includes taxes & fees 8.8/10 Excellent! (1,157 reviews) [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) Still don't see what you're looking for? [See all properties in South Side.](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=553248635074842823&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=553248635074842823&star=20&star=20&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=553248635074842823&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=553248635074842823&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=553248635074842823&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=08%2F10%2F2025&endDate=09%2F10%2F2025®ionId=553248635074842823&star=20&star=20&amenities=WATER_PARK) 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. ## Learn more about South Side Discover the metropolitan area of South Side—museums, skyscrapers and top sights like Lake Michigan. [See all hotels in South Side](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-21&endDate=2025-10-22&adults=2®ionId=553248635074842823) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26577-Museum-Of-Science-And-Industry.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top South Side Hotel Reviews ![Motel 6 - Chicago, IL](//images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg) ### Motel 6 - Chicago, IL 10/10 Excellent "Super nice update to the rooms. I was very impressed. Antonio at the front desk is phenomenal and very kind" [](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.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) ![Villa Dubois Guest House](//images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/e921e6b3_y.jpg) ### Villa Dubois Guest House 10/10 Excellent "Cool property, very safe with cams and code-locked door. No issues with noise, had a pretty quiet peaceful stay. Good parking situation, that’s something I was worried about but we never had problems parking. Unit is very close to transit lines. My girlfriend and I were out walking very late and never felt unsafe in this area. " [](https://expedia.co.uk/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) ![Skylark Motel](//images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/84aefbd3_y.jpg) ### Skylark Motel 6/10 Okay "Poorly cleaned and not kept up well." 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