Title: The 10 Best 2 Star Hotels in South Side - 2026 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) ![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 availability on South Side 2 Star Hotels Tonight [26 Feb - 27 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-26&endDate=2026-02-27&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [27 Feb - 28 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-27&endDate=2026-02-28&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-27&endDate=2026-03-01&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-03-06&endDate=2026-03-08&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side 2-star hotels ![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/1000000/210000/201300/201281/3dbc8b3d.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/1000000/210000/201300/201281/1d4ff2d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG [](https://www.expedia.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) Bedford Park 9.0/10 Wonderful (1,305 reviews) "The breakfast was good, and the shuttle bus was very convenient." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shuchen £89 includes taxes & fees 1 Mar - 2 Mar [](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/b32fc0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/16e59ea0.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) ![Towels](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/a0633f53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 - Chicago, IL [](https://www.expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) Washington Heights 7.2/10 Good (262 reviews) "Good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) NICHOLE £70 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Traditional Room, 2 Queen Beds, Non Smoking | Premium bedding, desk, laptop workspace, soundproofing](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/efb1181a.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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/26ad2ef6.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) ### Carlton Inn Midway [](https://www.expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) Archer Heights 6.4/10 (1,001 reviews) "It is a good place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul Adrian £77 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3456h2300x0y0-6e038619.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking (Jetted Tub) | Jetted bathtub](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3448h2304x4y0-e45070c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/w3451h2304x0y0-39d39828.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/c80663a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saratoga Motel By Capital O Near Midway Airport Chicago IL [](https://www.expedia.co.uk/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information) Ashburn 6.8/10 (36 reviews) "Great hosts" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John £64 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/d0c2eca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/5089d88a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/8d4eacf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/18e8c92a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Dubois Guest House [](https://www.expedia.co.uk/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) Bronzeville 8.6/10 Excellent (80 reviews) "My stay was very pleasant. The accommodation was comfortable, easily accessible, and well connected to public transport. I highly recommend it to anyone visiting the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lizeth £54 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.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) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/87403ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/ed5d1c61.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 [](https://www.expedia.co.uk/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) Burbank 6.6/10 (1,000 reviews) " Clean and quiet with a variety of restaurants nearby. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel £71 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.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/119000000/118840000/118831400/118831367/33faabf8.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) ![Front of property](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/ae5791b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capital O Empire Motel Chicago I-94 [](https://www.expedia.co.uk/Chicago-Hotels-Empire-Motel.h118831367.Hotel-Information) Greater Grand Crossing 3.2/10 (26 reviews) "I didn’t stay the establishment was boarded up " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kylen [](https://www.expedia.co.uk/Chicago-Hotels-Empire-Motel.h118831367.Hotel-Information) ![Room, 1 Queen Bed, Jetted Tub | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/2a2055fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, towels](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/62a8a4cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/dfae7ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Jetted Tub | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/132642eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rainbow Motel [](https://www.expedia.co.uk/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information) Garfield Ridge 5.6/10 (19 reviews) "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 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Conner [](https://www.expedia.co.uk/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/cdb6bc21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b66dd193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking | Desk, bed sheets](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/ea25cb66.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) ### Admiral Motel By Oyo Chicago I-94 [](https://www.expedia.co.uk/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) Chatham 4.2/10 (48 reviews) "Fine stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharmaine £66 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/919fb8df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self-parking, free valet parking](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/208b55cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/275d47ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/1cf69111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Motel By OYO Chicago I-90 [](https://www.expedia.co.uk/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) Woodlawn 3.6/10 (53 reviews) "Room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nyi £74 includes taxes & fees 6 Mar - 7 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) ![Free WiFi](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/a2a4ef31.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/953521af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Skylark Motel [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) Garfield Ridge 4.6/10 (120 reviews) "Easily one of the worst places ever. Slightly better than spending the night in Chicago Midway terminal." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen £72 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/18b54148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/e7c93e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/2b4e79c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/7043bce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Lake Shore Hotel [](https://www.expedia.co.uk/Chicago-Hotels-Ramada-Inn-Lake-Shore.h69827000.Hotel-Information) Kenwood 10/10 Exceptional (1 review) "Clean room but in need of renovation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irma [](https://www.expedia.co.uk/Chicago-Hotels-Ramada-Inn-Lake-Shore.h69827000.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/450ed27b.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/5bc8bb1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Chicago – Midway Airport S by IHG [](https://www.expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) West Lawn 8.4/10 Very good (1,002 reviews) "Staff very friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kali £97 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/cd4b36ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/7f723c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/fd997dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/0d444045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic. [](https://www.expedia.co.uk/Chicago-Hotels-Bronzeville-Jazz-Room-Beautiful.h121703532.Hotel-Information) Bronzeville 10/10 Exceptional (2 reviews) "The property was clean. The house was nice and neat. I enjoyed my stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lamyha S. [](https://www.expedia.co.uk/Chicago-Hotels-Bronzeville-Jazz-Room-Beautiful.h121703532.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/107000000/106880000/106875400/106875382/141e9606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106880000/106875400/106875382/a73bb442.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/107000000/106880000/106875400/106875382/34617f32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom apartment in awesome Chicago with WiFi, AC [](https://www.expedia.co.uk/Chicago-Hotels-Charming-2-Bedroom-Apartment-In-Awesome-Chicago-With-WiFi.h106875382.Hotel-Information) Gage Park [](https://www.expedia.co.uk/Chicago-Hotels-Charming-2-Bedroom-Apartment-In-Awesome-Chicago-With-WiFi.h106875382.Hotel-Information) ![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) ![Comfort Apartment | Free WiFi](https://images.trvl-media.com/lodging/120000000/119980000/119973600/119973593/206701c0.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/120000000/119980000/119973600/119973593/65b6e2ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Apartment near Chicago Downtown [](https://www.expedia.co.uk/Chicago-Hotels-Stylish-Apartment-Near-Chicago-Downtown.h119973593.Hotel-Information) Bridgeport 10/10 Exceptional (1 review) "When we arrived at the room, the access code didn’t work, so I contacted the host. Unfortunately, I didn’t get a response, so I had to reach out to support. It took two hours to get a response, and they informed me that the access code had been changed. This was quite frustrating. Once I got in, the room was amazing. It felt like I was at home. The only other complaints I have are the noisy furnace and the loud upstairs neighbors. The unit has quiet hours, but we were disturbed by the noise. I... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jada [](https://www.expedia.co.uk/Chicago-Hotels-Stylish-Apartment-Near-Chicago-Downtown.h119973593.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/d8f21990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/5806850d.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/106000000/105650000/105642800/105642745/26f3a1e7_edited_563b.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. [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Duplex-Obama-University-Chicago-Area-3BR.h105642745.Hotel-Information) Woodlawn 5.8/10 (6 reviews) "The house was absolutely beautiful ! Very spacious and nice! Comfy beds and clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandy W. [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Duplex-Obama-University-Chicago-Area-3BR.h105642745.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/107000000/106550000/106543700/106543613/7ce91cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106550000/106543700/106543613/11e19a02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Landmark; a comfy suite near McCormick Place [](https://www.expedia.co.uk/Chicago-Hotels-The-Landmark-A-Comfy-Suite-Near-McCormick-Place.h106543613.Hotel-Information) Bronzeville 10/10 Exceptional (9 reviews) "A great place to stay! Host was amazing and gave great recommendations on things to do. The space was clean and perfect for our weekend getaway!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Porsche M. [](https://www.expedia.co.uk/Chicago-Hotels-The-Landmark-A-Comfy-Suite-Near-McCormick-Place.h106543613.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) ![Dining](https://images.trvl-media.com/lodging/107000000/106770000/106765300/106765283/f4efcf80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106770000/106765300/106765283/b9bfc402.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) ### Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games! [](https://www.expedia.co.uk/Chicago-Hotels-Gorgeous-5-Bedroom-Gem-Sleeps-18-With-Pool.h106765283.Hotel-Information) Auburn Gresham 10/10 Exceptional (1 review) "Great lot of space " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) phyllis d. [](https://www.expedia.co.uk/Chicago-Hotels-Gorgeous-5-Bedroom-Gem-Sleeps-18-With-Pool.h106765283.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/1050258f.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) ![Interior](https://images.trvl-media.com/lodging/108000000/107100000/107095000/107094905/e4969ce4.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/108000000/107100000/107095000/107094905/5d21d940.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-1-Bedroom-Apartment-With-WiFi.h107094905.Hotel-Information) Bronzeville 9.8/10 Exceptional (15 reviews) "Oŵner was great! I will definitely stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven M. [](https://www.expedia.co.uk/Chicago-Hotels-Cozy-1-Bedroom-Apartment-With-WiFi.h107094905.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. ![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 £102 5 Mar - 6 Mar includes taxes & fees 9.6/10 Exceptional! (1,000 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 £85 2 Mar - 3 Mar includes taxes & fees 8.8/10 Excellent! (1,176 reviews) [](https://expedia.co.uk/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![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 £117 5 Mar - 6 Mar includes taxes & fees 8.8/10 Excellent! (1,000 reviews) [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.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=28%2F02%2F2026&endDate=01%2F03%2F2026®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=28%2F02%2F2026&endDate=01%2F03%2F2026®ionId=553248635074842823&star=20&star=20&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F02%2F2026&endDate=01%2F03%2F2026®ionId=553248635074842823&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F02%2F2026&endDate=01%2F03%2F2026®ionId=553248635074842823&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F02%2F2026&endDate=01%2F03%2F2026®ionId=553248635074842823&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F02%2F2026&endDate=01%2F03%2F2026®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=2026-03-13&endDate=2026-03-14&adults=2®ionId=553248635074842823) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=900&h=514&p=1&q=high) ## Top South Side Hotel Reviews ![Motel 6 - Chicago, IL](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/55e03c95_y.jpg) ### Motel 6 - Chicago, IL 10/10 Excellent "Mrs Wilson is the best" [](https://expedia.co.uk/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "Clean room. Professional and courteous staff" [](https://expedia.co.uk/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) ![Rainbow Motel](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/5c5ac2f3_y.jpg) ### Rainbow Motel 10/10 Excellent "At one point, Rainbow Motel.may have been down, but the new owners are worki g to turn the experience around. What you get: a clean room with TV and a comfortable bed and shower. But, youre also RIGHT across from arguably one of the BEST bakeries in the country (Weber's Bakery -fresh morning sonuts and pastries), around the corner from Chicago's most popular beef sandwich (Portillo's), within a 2 minute walk of several other restaurants as well as an Aldi, Walgreens and Ace Hardware. BUT... the big perk is a stop on the Archer line out front 50' away. (also a late night bus if you do a late Chocago night) and 1.5 mins walk from the OHare (330) bus. These things made it an ideal cheap stay in a clean room for someone who flew in and out with no car for a music festival. It was SUPER easy to get around and time transit. And dont overlook that late night bus perk. That said, if this is a family vacation, do your homework, but it was an easy yes for a single or couple of adults travelling on a budget. " [](https://expedia.co.uk/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information) ## Find out more about South Side ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - More ways to book - [1 Star Hotels in Chicago ](https://www.expedia.co.uk/1Star-Chicago-Hotels.s10-0-d178248.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Chicago ](https://www.expedia.co.uk/2Star-Chicago-Hotels.s20-0-d178248.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Northwest Side ](https://www.expedia.co.uk/2Star-Northwest-Side-Hotels.s20-0-d553248635976475367.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Chicago ](https://www.expedia.co.uk/3Star-Chicago-Hotels.s30-0-d178248.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Elmhurst ](https://www.expedia.co.uk/3Star-Elmhurst-Hotels.s30-0-d7836.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Lincoln Park ](https://www.expedia.co.uk/3Star-Lincoln-Park-Chicago-Hotels.s30-n6059328-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in The Loop ](https://www.expedia.co.uk/3Star-The-Loop-Chicago-Hotels.s30-n800024-0.Travel-Guide-Filter-Hotels) - 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