Title: TOP Hotels with Connecting Rooms in South Side, IL for 2025 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26577-Museum-Of-Science-And-Industry.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Hotels with Connecting Rooms in South Side ![](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 Connecting Rooms Tonight [27 Oct - 28 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-27&endDate=2025-10-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [28 Oct - 29 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [31 Oct - 2 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [7 Nov - 9 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top South Side Hotels with Connecting Rooms ![View from property](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/a475d71a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet breakfast on weekends (USD 26.00 per person)](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/04630218.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/900000/892200/892168/67f6b752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Marriott Midway Bedford Park 8.4/10 Very good (903) "Very clean and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Louis £128 includes taxes & fees 11 Nov - 12 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/210000/201300/201281/65c30d17.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) ![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 | 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) ### Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG Bedford Park 9.0/10 Wonderful (1162) "Room was spacious and clean. Breakfast was nice and convenient. Will stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Esther £112 includes taxes & fees 18 Nov - 19 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Holiday-Inn-Express-Hotel-Suites-Chicago-Midway-Airport.h201281.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/e1b9cc64.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) ![Desk, laptop workspace, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/2f40f114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Chicago Chinatown Chinatown 9.6/10 Exceptional (1025) "Room was very clean, staff extremely friendly, and great dining options. Would stay there again in the future." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Osama £102 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Chicago-Hotels-SpringHill-Suites-By-Marriott-Chicago-Chinatown.h64624399.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) ![Daily buffet breakfast (USD 11 per person)](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/4c3ef871.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/517a0e3d.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 Hyde Park 8.8/10 Excellent (1025) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nikhil £127 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f98af4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/8f681739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/f1fd01e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/b456698d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sophy Hyde Park Hyde Park 9.6/10 Exceptional (1007) "Loved my stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawnielle £186 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/01c93cca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (2045) "Great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ron £111 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/fb110cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Lake View | 1 bedroom, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2695x3y3-e619dd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chicago Downtown Chicago 9.4/10 Exceptional (3369) "Great location and hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Travis £145 includes taxes & fees 26 Nov - 27 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (2227) "Rooms were clean with a great view of the lake and the city " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan £111 includes taxes & fees 25 Nov - 26 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2876) "Had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josh £95 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/023ff9a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/43039f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room | 1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago Downtown Chicago 8.4/10 Very good (2940) "Nice hotel close to everything Enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara £89 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.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=2025-11-11&endDate=2025-11-12®ionId=553248635074842823&adults=2&room_amenities_group_explore=connecting_rooms_available&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![Hyatt Place Chicago-South/University Medical Center](//images.trvl-media.com/lodging/7000000/6060000/6059100/6059069/722a9f0a_y.jpg) ### Hyatt Place Chicago-South/University Medical Center 10/10 Excellent "Just an overnight stay for a college campus visit, but had the Hyatt recommended by numerous people and it didn't disappoint. What a great community the Hyde Park area was. Rooms were very nice, big and extremely clean. Will definitely be making that out go to for all future trips to the Chicago land area" [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chicago Marriott Midway](//images.trvl-media.com/lodging/1000000/900000/892200/892168/99523df7_y.jpg) ### Chicago Marriott Midway 10/10 Excellent "Our stay was hassle free. The room was immaculate. The staff was helpful and courteous. " [](https://expedia.co.uk/Chicago-Hotels-Chicago-Marriott-Midway.h892168.Hotel-Information) ![Best Western Inn & Suites - Midway Airport](//images.trvl-media.com/lodging/1000000/520000/517500/517495/92ee0c20_y.jpg) ### Best Western Inn & Suites - Midway Airport 10/10 Excellent "The outside didn't do it justice. We pulled up thinking it looked horrible, but as soon as we went inside it was amazing. Very modern and nicely modeled. The breakfast was amazing and sealed it. The cheese omelette hit the spot and the way pancake maker was an awesome thing for the kid. I would for sure stay here again if l came back to Chicago." 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[Gay-Friendly Hotels in Gage Park](https://www.expedia.co.uk/Gage-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132375-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in Grand Boulevard](https://www.expedia.co.uk/Grand-Boulevard-Chicago-Hotels-Business-Hotel.0-n6132310-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Greater Grand Crossing Hotels](https://www.expedia.co.uk/Greater-Grand-Crossing-Chicago-Hotels.0-n6132273-0.Travel-Guide-Filter-Hotels) - [Hotels near Hyde Park Art Center](https://www.expedia.co.uk/Hyde-Park-Art-Center-Hotels.0-l553248621533116337-0.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Hyde Park](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Beach-Hotels.0-n117842-0-tBeachHotels.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Hyde Park](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n117842-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Hyde Park](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Golf-Hotels.0-n117842-0-tGolfHotels.Travel-Guide-Filter-Hotels) - 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[Mckinley Park Hotels](https://www.expedia.co.uk/McKinley-Park-Chicago-Hotels.0-n6132389-0.Travel-Guide-Filter-Hotels) - [Casino Hotels in Near South Side](https://www.expedia.co.uk/Near-South-Side-Chicago-Hotels-Casino-Hotel.0-n6132399-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Near South Side Hotels](https://www.expedia.co.uk/Near-South-Side-Chicago-Hotels.0-n6132399-0.Travel-Guide-Filter-Hotels) - [Oakland Hotels](https://www.expedia.co.uk/Oakland-Chicago-Hotels.0-n6132392-0.Travel-Guide-Filter-Hotels) - [Hotels near Robert W Roloson Houses](https://www.expedia.co.uk/Robert-W-Roloson-Houses-Hotels.0-l553248621533116343-0.Travel-Guide-Filter-Hotels) - [Hotels near SR Crown Hall](https://www.expedia.co.uk/SR-Crown-Hall-Hotels.0-l553248621533116346-0.Travel-Guide-Filter-Hotels) - [Hotels near Soldier Field](https://www.expedia.co.uk/Soldier-Field-Hotels.0-l6058043-0.Travel-Guide-Filter-Hotels) - [South Loop Hotels](https://www.expedia.co.uk/South-Loop-Chicago-Hotels.0-n6130108-0.Travel-Guide-Filter-Hotels) - [South Shore Hotels](https://www.expedia.co.uk/South-Shore-Chicago-Hotels.0-n6132437-0.Travel-Guide-Filter-Hotels) - [Apartments in Southwest Side](https://www.expedia.co.uk/Southwest-Side-Apartments.d553248635976475403-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Southwest Side](https://www.expedia.co.uk/Southwest-Side-Cabins.d553248635976475403-aaCabins.Travel-Guide-Accommodation) - [Hotels near University of Chicago](https://www.expedia.co.uk/University-Of-Chicago-Hotels.0-l6064081-0.Travel-Guide-Filter-Hotels) - [Washington Park Hotels](https://www.expedia.co.uk/Washington-Park-Chicago-Hotels.0-n171466-0.Travel-Guide-Filter-Hotels) - [West Englewood Hotels](https://www.expedia.co.uk/West-Englewood-Chicago-Hotels.0-n6132412-0.Travel-Guide-Filter-Hotels) - [Hotels near Wintrust Arena](https://www.expedia.co.uk/Wintrust-Arena-Hotels.0-l553248634328853320-0.Travel-Guide-Filter-Hotels) - [Flights to Chicago](https://www.expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to Southwest Side](https://www.expedia.co.uk/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights) - [Visit Grand Boulevard](https://www.expedia.co.uk/Chicago-Grand-Boulevard.dx6132310) - [Visit Hyde Park](https://www.expedia.co.uk/Chicago-Hyde-Park.dx117842) - [Visit Jackson Park Highlands](https://www.expedia.co.uk/Chicago-Jackson-Park-Highlands.dx6132329) - [Visit Near South Side](https://www.expedia.co.uk/Chicago-Near-South-Side.dx6132399) - [Visit Prairie District](https://www.expedia.co.uk/Chicago-Prairie-District.dx553248635976473159) - [Visit South Commons](https://www.expedia.co.uk/Chicago-South-Commons.dx6132263) - [Visit South Loop](https://www.expedia.co.uk/Chicago-South-Loop.dx6130108) - [Chicago Holidays](https://www.expedia.co.uk/Chicago.d178248.Holidays-City-Breaks) - [Essex Holidays](https://www.expedia.co.uk/Essex.d6132371.Holidays-City-Breaks) - [Hyde Park Holidays](https://www.expedia.co.uk/Hyde-Park.d117842.Holidays-City-Breaks) - [Robie House](https://www.expedia.co.uk/Robie-House-Hyde-Park.d6064059.Attraction) - [Sr Crown Hall](https://www.expedia.co.uk/SR-Crown-Hall-Bronzeville.d553248621533116346.Attraction) - [S.s. Peter and Paul Church](https://www.expedia.co.uk/SS-Peter-And-Paul-Church-McKinley-Park.d6247219.Attraction) - [Car hire near Lake Meadows Park](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lake-Meadows-Park.d6132351.Car-Hire-Guide) - [Enterprise Rental Cars in Hyde Park](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Hyde-Park.d117842-c15.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Southwest Side](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Southwest-Side.d553248635976475403-c15.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Hyde Park](https://www.expedia.co.uk/Europcar-Car-Rentals-In-Hyde-Park.d117842-c14.Car-Rental-Guide-Suppliers) - [Book Hotels with Connecting Rooms in South Side on Expedia.com](https://www.expedia.com/South-Side-Hotels-Hotels-With-Adjoining-Rooms.0-0-d553248635074842823-tHotelswithAdjoiningRooms.Travel-Guide-Filter-Hotels)