Title: 2 Stars Hotels in South Side, Chicago from CA $112 - Find Cheap South Side Hotels With 2 Stars | Expedia.ca [South Side Travel Guide](https://expedia.ca/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.ca/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.ca/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.ca/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide)[South Side Vacation Packages](https://expedia.ca/South-Side.d553248635074842823.Destination-Travel-Guides) ![I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck. ](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Richard Remington # 2 Stars Hotels in South Side, Chicago from CA $112 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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 [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-11&endDate=2025-12-12&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-13&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-12&endDate=2025-12-14&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-19&endDate=2025-12-21&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/1000000/210000/201300/201281/1d4ff2d0.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) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/f80081f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) Bedford Park 9.0/10 Wonderful (1232) "Will definitely stay there again ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose Remedios CA $154 CA $181 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/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/d12ffd97.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) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/bdc72fec.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.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) Washington Heights 7.0/10 Good (200) "Everything was very nice even staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maurice CA $99 CA $116 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.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 tub](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.ca/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.Hotel-Information) Ashburn 7.0/10 Good (29) "Clean room friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $94 CA $121 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/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/36000000/35550000/35542300/35542249/994a5eaa.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) ![Full-size 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) ### Villa Dubois Guest House [](https://www.expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.Hotel-Information) Bronzeville 8.6/10 Excellent (78) "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 CA $95 CA $112 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/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) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/a537c55a.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) ### Best Western Inn & Suites - Midway Airport [](https://www.expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) Burbank 6.6/10 (1000) "Room was very clean and staff did a great job at upkeeping. Not too far from Midway airport where you can use the CTA to get downtown if needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Markus CA $132 CA $147 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/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) ![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) ![Bed sheets](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/33faabf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free toiletries, towels](https://images.trvl-media.com/lodging/119000000/118840000/118831400/118831367/0d671bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Capital O Empire Motel Chicago I-94 [](https://www.expedia.ca/Chicago-Hotels-Empire-Motel.h118831367.Hotel-Information) Greater Grand Crossing 3.2/10 (26) "They were closed when I got there." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carter [](https://www.expedia.ca/Chicago-Hotels-Empire-Motel.h118831367.Hotel-Information) ![Room, 1 Queen Bed, Jetted Tub](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/2a2055fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Jetted Tub](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/132642eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/116000000/115350000/115345700/115345673/dfae7ccf.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) ### Rainbow Motel [](https://www.expedia.ca/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information) Garfield Ridge 5.8/10 (18) "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 CA $134 CA $171 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/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) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/ea25cb66.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) ![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.ca/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) Chatham 3.8/10 (45) "Fine stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharmaine CA $104 CA $131 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/ab261a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/30d5c7e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/19cdbb10.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) ### Best Motel By OYO Chicago I-90 [](https://www.expedia.ca/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) Woodlawn 3.4/10 (48) "Clean room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pierre [](https://www.expedia.ca/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/38fe6f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-refrigerator](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/b118c2d6.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.ca/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) Garfield Ridge 4.6/10 (119) "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 CA $114 CA $134 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) ![Room](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/9547c5c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/6498b45e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/9cce10bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/70000000/69830000/69827000/69827000/0b280cdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Lake Shore Hotel [](https://www.expedia.ca/Chicago-Hotels-Chicago-Lake-Shore-Hotel.h69827000.Hotel-Information) Kenwood 10/10 Exceptional (1) "Clean room but in need of renovation " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Irma [](https://www.expedia.ca/Chicago-Hotels-Chicago-Lake-Shore-Hotel.h69827000.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) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/8d1ccba4.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) ![Exterior](https://images.trvl-media.com/lodging/122000000/121710000/121703600/121703532/7f723c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bronzeville Jazz Room. Beautiful, cozy, centered, relaxing, rustic. [](https://www.expedia.ca/Chicago-Hotels-Bronzeville-Jazz-Room-Beautiful.h121703532.Hotel-Information) Bronzeville 10/10 Exceptional (1) "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.ca/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) ![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) ![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 [](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-Apartment-In-Awesome-Chicago-With-WiFi.h106875382.Hotel-Information) Gage Park [](https://www.expedia.ca/Chicago-Hotels-Charming-2-Bedroom-Apartment-In-Awesome-Chicago-With-WiFi.h106875382.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) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105650000/105642800/105642745/26f3a1e7_edited_563b.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) ![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) ### Modern Duplex-Obama & University Chicago Area 3BR, 2.5Bath. Enjoy entire unit. [](https://www.expedia.ca/Chicago-Hotels-Modern-Duplex-Obama-University-Chicago-Area-3BR.h105642745.Hotel-Information) Woodlawn 5.8/10 (6) "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.ca/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) ![Interior](https://images.trvl-media.com/lodging/107000000/106550000/106543700/106543613/11e19a02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106550000/106543700/106543613/05742c20.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 [](https://www.expedia.ca/Chicago-Hotels-The-Landmark-A-Comfy-Suite-Near-McCormick-Place.h106543613.Hotel-Information) Bronzeville 10/10 Exceptional (8) "A lovely place to rest after busy days in Chicago! Quiet and clean with all that is needed to catch-up with yourself." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate D. [](https://www.expedia.ca/Chicago-Hotels-The-Landmark-A-Comfy-Suite-Near-McCormick-Place.h106543613.Hotel-Information) ![Smart TV, fireplace, video games, foosball](https://images.trvl-media.com/lodging/107000000/106770000/106765300/106765283/5f0dbb32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106770000/106765300/106765283/f1726b5a.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) ### Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games! [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-5-Bedroom-Gem-Sleeps-18-With-Pool.h106765283.Hotel-Information) Auburn Gresham 10/10 Exceptional (1) "Great lot of space " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) phyllis d. [](https://www.expedia.ca/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/e4969ce4.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) ### Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago [](https://www.expedia.ca/Chicago-Hotels-Cozy-1-Bedroom-Apartment-With-WiFi.h107094905.Hotel-Information) Bronzeville 9.8/10 Exceptional (14) "I really enjoyed my stay. Host was very nice and attentive. The place was clean and cozy. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley M. [](https://www.expedia.ca/Chicago-Hotels-Cozy-1-Bedroom-Apartment-With-WiFi.h107094905.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/121000000/120770000/120762600/120762567/b51be452.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/121000000/120770000/120762600/120762567/648e6fc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120770000/120762600/120762567/c32fd0bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120770000/120762600/120762567/dd4a4141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic feel, Modern comfort Walk to parks and food in beautiful Chicago [](https://www.expedia.ca/Chicago-Hotels-Historic-Feel.h120762567.Hotel-Information) Brighton Park 10/10 Exceptional (2) "Great spot, very easy! Having your own parking spot in a garage is very nice too so you don't have to deal with street parking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel B. [](https://www.expedia.ca/Chicago-Hotels-Historic-Feel.h120762567.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/109000000/108430000/108420500/108420492/35d1561d.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/109000000/108430000/108420500/108420492/2e53223a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108430000/108420500/108420492/242c0360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous 4BDR in Chicago / 15mins from DWTN Brand New! [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-4BDR-In-Chicago-15mins-From-DWTN-Brand-New.h108420492.Hotel-Information) South Shore 10/10 Exceptional (3) "10/10 very clean very nice looks just like the pictures " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) QKING D. [](https://www.expedia.ca/Chicago-Hotels-Gorgeous-4BDR-In-Chicago-15mins-From-DWTN-Brand-New.h108420492.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109370000/109364400/109364310/e167cf45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109370000/109364400/109364310/bbdf2c04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109370000/109364400/109364310/520e0125.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) ### Cozy 3-bedroom condo near University of Chicago [](https://www.expedia.ca/Chicago-Hotels-Cozy-3-Bedroom-Condo-Near-University-Of-Chicago.h109364310.Hotel-Information) Woodlawn 10/10 Exceptional (2) "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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deb C. [](https://www.expedia.ca/Chicago-Hotels-Cozy-3-Bedroom-Condo-Near-University-Of-Chicago.h109364310.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.ca/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.ca/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 CA $154 CA $181 total Jan 2 - Jan 3, 2026 includes taxes & fees 9.4/10 Exceptional! (1,009 reviews) [](https://expedia.ca/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 CA $171 CA $201 total Dec 13 - Dec 14 includes taxes & fees 8.8/10 Excellent! (1,178 reviews) [](https://expedia.ca/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 CA $175 CA $206 total Dec 19 - Dec 20 includes taxes & fees 8.6/10 Excellent! (1,004 reviews) [](https://expedia.ca/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.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=553248635074842823&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=553248635074842823&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=553248635074842823&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=553248635074842823&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=553248635074842823&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F12%2F2025&endDate=14%2F12%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.ca/Hotel-Search?startDate=2025-12-26&endDate=2025-12-27&adults=2®ionId=553248635074842823) ![I thought Wood Ducks were the most amazingly colorful and photogenic ducks until I spotted this incredible bird on the lakefront. What a handsome beautiful duck. ](https://images.trvl-media.com/place/829/3b8962fc-94e7-486b-84ab-96e09a77459b.jpg?impolicy=fcrop&w=900&h=590&p=1&q=high) Photo by Richard Remington ## Top South Side Hotel Reviews ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "Staff is great, clean rooms " [](https://expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.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 "Great stay" [](https://expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![Villa Dubois Guest House](https://images.trvl-media.com/lodging/36000000/35550000/35542300/35542249/e921e6b3_y.jpg) ### Villa Dubois Guest House 10/10 Excellent "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." [](https://expedia.ca/Chicago-Hotels-Villa-Dubois-Guest-House.h35542249.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.ca/Chicago-Hotels-Rainbow-Motel.h115345673.Hotel-Information) ![Skylark Motel](https://images.trvl-media.com/lodging/2000000/1660000/1658500/1658428/84aefbd3_y.jpg) ### Skylark Motel 6/10 Okay "Poorly cleaned and not kept up well." [](https://expedia.ca/Chicago-Hotels-Skylark-Motel.h1658428.Hotel-Information) ## Find out more about South Side Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in South Side, South Side you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions. Several of the best hotels with 2 Stars in South Side are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. You won’t believe how inexpensive your next vacation can be when you settle in at a top two star hotel in South Side. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [1 Star Hotels in Chicago ](https://www.expedia.ca/1Star-Chicago-Hotels.s10-0-d178248.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Far Southwest Side ](https://www.expedia.ca/1Star-Far-Southwest-Side-Hotels.s10-0-d553248635976475353.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Gano ](https://www.expedia.ca/1Star-Gano-Chicago-Hotels.s10-n6132380-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Grace Abbott Homes ](https://www.expedia.ca/1Star-Grace-Abbott-Homes-Chicago-Hotels.s10-n6132393-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Sheffield and DePaul ](https://www.expedia.ca/1Star-Sheffield-And-DePaul-Chicago-Hotels.s10-n553248635976474890-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in South Englewood ](https://www.expedia.ca/1Star-South-Englewood-Chicago-Hotels.s10-n6132433-0.Travel-Guide-Filter-Hotels) - 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