Title: TOP Hotels with Babysitting Services in South Side, IL for 2026 | 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 Hotels with Babysitting Services Tonight [28 Jan - 29 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [29 Jan - 30 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [6 Feb - 8 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South Side hotels with childcare ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two Queen Beds Room | Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/d04bec0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/a9fdeea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) Downtown Chicago 8.6/10 Excellent (3,032 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Omar £78 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/b9c16475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/d35b9e24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/f4944277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17809/54e0cfd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chicago Hotel Collection Ambassador Gold Coast [](https://www.expedia.co.uk/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information) Downtown Chicago 8.2/10 Very good (1,278 reviews) "Great hotel at an affordable price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dhruv £98 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Chicago-Hotels-The-Chicago-Hotel-Collection-Ambassador-Gold-Coast.h17809.Hotel-Information) ![Executive lounge](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, pillow-top beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7915e59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/84fcc5bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fairmont Gold, Suite, 1 King Bed, Accessible | Premium bedding, down duvets, pillow-top beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/3b05bc98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairmont Chicago at Millennium Park [](https://www.expedia.co.uk/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,050 reviews) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vonzell £169 includes taxes & fees 29 Jan - 30 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Fairmont-Chicago-At-Millennium-Park.h15937.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Café](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/b6033176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/b59ebdf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/95d420ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pendry Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (1,144 reviews) "Excellent hotel and location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcelo £174 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/97bbd3be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | Living area | 37-inch LCD TV with cable channels, Smart TV](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/4eb87158.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/d83a4f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | View from room](https://images.trvl-media.com/lodging/1000000/20000/10700/10607/3bc31c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Chicago Downtown/Magnificent Mile [](https://www.expedia.co.uk/Chicago-Hotels-Hampton-Inn-Chicago-DowntownMagnificent-Mile.h10607.Hotel-Information) Downtown Chicago 8.0/10 Very good (1,390 reviews) "Great hotel,, like so much" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ilham £76 includes taxes & fees 3 Feb - 4 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Hampton-Inn-Chicago-DowntownMagnificent-Mile.h10607.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/69dc07eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Penthouse (Suite) | Egyptian cotton sheets, premium bedding, down duvets, minibar](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/e0860a68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Penthouse (Suite) | City view](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/c6969482.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/0a9fe031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Viceroy Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Viceroy-Chicago.h18614145.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,161 reviews) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allyson £199 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Viceroy-Chicago.h18614145.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c35e7743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Body treatments, body wraps, body scrubs, facials](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/838eb9bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c665b589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trump International Hotel & Tower Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,828 reviews) "Exceptional service, great location, beautiful hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie £245 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/d1b25ed0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/dfd1e89b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pet-friendly](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/c2c59838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,000 reviews) "Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Glenn £323 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/acbf2aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/5616df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/bbac06a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago [](https://www.expedia.co.uk/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) Downtown Chicago 9.8/10 Exceptional (1,013 reviews) "The best hotel ! Always pleasant to stay ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maysa £403 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) ![Rooftop bar](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/9f7255de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/657cdd36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/baa44a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/10000000/9060000/9059600/9059537/cdaa71fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Loews Chicago Hotel [](https://www.expedia.co.uk/Chicago-Hotels-Loews-Chicago-Hotel.h9059537.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,588 reviews) "Outstanding location great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael £177 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Loews-Chicago-Hotel.h9059537.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.co.uk/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12®ionId=553248635074842823&adults=2&property_amenities_group_explore=babysitting_or_childcare&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - More ways to book - [4 Star Hotels in McKinley Park ](https://www.expedia.co.uk/4Star-McKinley-Park-Chicago-Hotels.s40-n6132389-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in New City ](https://www.expedia.co.uk/5Star-New-City-Chicago-Hotels.s50-n6132388-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Armour Square ](https://www.expedia.co.uk/Armour-Square-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132365-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Avalon Park ](https://www.expedia.co.uk/Avalon-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132379-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Bridgeport Hotels ](https://www.expedia.co.uk/Bridgeport-Chicago-Hotels.0-n6132075-0.Travel-Guide-Filter-Hotels) - 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