Title: Book the Best South Side Hotels with FREE WIFI in 2026 | 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) ![Chicago South Side](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with Wifi in South Side, IL from CA $116 - ![](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 Hotels with Wifi Tonight [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-13&endDate=2025-12-14&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-14&endDate=2025-12-15&adults=2&amenities=WIFI&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&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side hotels with wifi ![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) ![Reception](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/c80663a4.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) ![Free self parking](https://images.trvl-media.com/lodging/122000000/121180000/121175100/121175039/ed8b3d68.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 $118 CA $150 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Chicago-Hotels-Saratoga-Motel-By-Capital-O-Chicago-Midway-IL-US-12.h121175039.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) ![Towels](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/a0633f53.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 [](https://www.expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) Washington Heights 7.0/10 Good (203) "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 15 - Dec 16 [](https://www.expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Living room](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/8ed533e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/816d88c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/28814a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jaslin Hotel [](https://www.expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) Chinatown 9.0/10 Wonderful (1183) "Excellent service, clean room, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefan CA $178 CA $209 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/e3b5efe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/5ab28ea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/4f69d6e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Chicago-South/University Medical Center [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) Hyde Park 8.8/10 Excellent (1002) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nikhil CA $186 CA $218 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/bf40a417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/69b37e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/3123fdae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Chicago Chinatown [](https://www.expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) Chinatown 9.6/10 Exceptional (1001) "Clean, good staff" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Veronique E CA $154 CA $181 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/3dbc8b3d.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 8.8/10 Excellent (1234) "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) ![Smart TV, video games](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-166f73c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1350h899x0y1-09740a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/w1278h1921x2y2-bce03282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91090000/91086500/91086437/2b5be5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6 [](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information) Brighton Park 8.6/10 Excellent (20) "Clean and nice. My son loved the arcade game. Would stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nichole S. CA $83 CA $280 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chicago-Hotels-Sunflower-Apt-12-Min-From-Downtown-CHI.h91086437.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/cf195af6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/7d0f8c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/fe86e080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792489/dd9a1f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleek & Functional 2-Bedroom Apt [](https://www.expedia.ca/Chicago-Hotels-Sleek-Functional-2-Bedroom-Apt.h116792489.Hotel-Information) Hyde Park 9.6/10 Exceptional (4) "Nice place for a girls trip weekend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madonna A. CA $87 CA $253 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Sleek-Functional-2-Bedroom-Apt.h116792489.Hotel-Information) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/e1aa934f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/cc47c33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/829bcf7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793083/d10b773f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Studio Near UChicago [](https://www.expedia.ca/Chicago-Hotels-Modern-Studio-Near-UChicago.h116793083.Hotel-Information) Hyde Park 9.6/10 Exceptional (11) "Clean room and convenient location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gabriela CA $83 CA $213 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Modern-Studio-Near-UChicago.h116793083.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/75d1dc95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/0d5faef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/5f21f45c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792500/116792457/c4d843cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright 1BR Unit in a Prime Spot [](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-Gem-In-Chicago-Kenwood-501.h116792457.Hotel-Information) Hyde Park 10/10 Exceptional (1) "We had a great stay. Location is in nice neighborhood with walking access to restaurants and university of Chicago. Apartment was clean and as pictured. Would stay again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) christine m. CA $83 CA $227 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Chicago-Hotels-Modern-1BR-Gem-In-Chicago-Kenwood-501.h116792457.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.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29®ionId=553248635074842823&adults=2&amenities=WIFI&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17_y.jpg) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG 10/10 Excellent "Breakfast was good and plenty of food. Shuttle was -- thank goodness because it was COLD -- timely!" [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg) ### Jaslin Hotel 10/10 Excellent "Everything is good " [](https://expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "y" [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![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) ![Hyatt Place Chicago-South/University Medical Center](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "Kim, at the front desk,was welcoming and helpful. She was sooooo kind and considerate!" [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Very convenient and clean and friendly! " [](https://expedia.ca/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "Hotel and room was very clean and the desk clerk was courteous " [](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.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." 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