Title: Book the Best South Side FAMILY FRIENDLY Hotels from CA $116 - Kid-Friendly Hotels in South Side, IL | 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) ![](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__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 Family Hotels Tonight [Jan 24 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-24&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Jan 25 - Jan 26](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-25&endDate=2026-01-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) In two weeks [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for South Side family-friendly hotels ![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) ![Lobby](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/0fb0f5ac.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) ![Hallway](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/816d88c5.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 8.8/10 Excellent (1,177 reviews) "Great service and clean roomd" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) evelina CA $128 CA $151 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Chicago-Hotels-Jaslin-Hotel.h13320264.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) ![Towels](https://images.trvl-media.com/lodging/116000000/115880000/115871700/115871645/a0633f53.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) ### Motel 6 - Chicago, IL [](https://www.expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.Hotel-Information) Washington Heights 7.0/10 Good (234 reviews) "The staff are wonderful and vigilant" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roxanne CA $99 CA $116 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Chicago-Hotels-Motel-6-Chicago.h115871645.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.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) West Lawn 8.4/10 Very good (1,001 reviews) "Friendly staff and clean room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alisa CA $134 CA $171 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/ddd4f59a.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) ### 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 (1,007 reviews) "Staff was very helpful and my stay was wonderful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Delonna CA $185 CA $217 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Traditional Room, 2 Queen Beds, Non Smoking](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) ![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/3000000/2950000/2949200/2949171/26ad2ef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carlton Inn Midway [](https://www.expedia.ca/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 CA $121 CA $142 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/520000/517500/517495/ff20a621.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) ### 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 (1,001 reviews) " Clean and quiet with a variety of restaurants nearby. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $131 CA $146 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/c9bd722f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, in-room safe, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/11170f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/d31527c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111910000/111903200/111903171/eedcca40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Retreat, Chic Retreat "Your Urban Getaway" [](https://www.expedia.ca/Chicago-Hotels-Chic-Retreat.h111903171.Hotel-Information) Roseland 6.0/10 (4 reviews) "The host was excellent and she responded to all my questions in an excellent manner. The home was beautiful as pictured. I wouldn’t mind staying there again on my next visit! I parked my car out in front and was no problems the 3 days we were there! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keiona W. CA $342 CA $536 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Chicago-Hotels-Chic-Retreat.h111903171.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) ![Desk, bed sheets](https://images.trvl-media.com/lodging/14000000/13280000/13279200/13279118/fba78af5.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) ![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) ### Best Motel By OYO Chicago I-90 [](https://www.expedia.ca/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.Hotel-Information) Woodlawn 3.6/10 (52 reviews) "Room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nyi [](https://www.expedia.ca/Chicago-Hotels-Best-Motel-By-OYO-Chicago-I-90.h13279118.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) ![Property entrance](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b1d231c1.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) ![Lobby](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/b66dd193.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 (46 reviews) "Fine stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharmaine [](https://www.expedia.ca/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/dfb99e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/d37889fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e7ca688f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Hotel [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) Downtown Chicago 8.8/10 Excellent (4,957 reviews) "Great stay, good location, accommodating staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ian CA $118 CA $139 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.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=2026-02-07&endDate=2026-02-08®ionId=553248635074842823&adults=2&travelerType=family_friendly&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 "Room was spotless, staff was great. Would definitely stay here again " [](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 "Clean room. Friendly & helpful staff. Convenient location. " [](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) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "All great!" [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/w3836h2161x5y0-7f85e9e1_y.jpg) ### Holiday Inn Chicago – Midway Airport S by IHG 10/10 Excellent "I was greeted with a smile we checking our room and we were late. They were very accommodating. They have a bar which we went over to eat from. I don’t know the bartender’s real name we were cold to call her TT. She was the very best ever very kind very sociable and friendly. I will be returning to this property the next time I’m in Chicago. I really had a great experience at this hotel with the staff is also includes the manager the hotel clerk, as well as the security guard. I will give my experience at this hotel five stars." [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-Mall-Area-Mdw-Arpt-S.h2190.Hotel-Information) ![Chinatown Hotel Chicago](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Get what you pay for! " [](https://expedia.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ![Chicago Marriott Midway](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Spent a night! Wish I could have stayed longer. The space was clean and beautifully designed, and the hotel staff were extremely accommodating to my needs. Wish I had gotten to enjoy the menu items, but I had to get back to the airport. The shuttle was also great; it came every 20 minutes, and I loved saving money on ride-sharing back to the airport in the morning. Overall great! " [](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 "Courteous staff. Clean rooms." [](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![Carlton Inn Midway](https://images.trvl-media.com/lodging/3000000/2950000/2949200/2949171/f9196562_y.jpg) ### Carlton Inn Midway 10/10 Excellent "It is a good place to stay." 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