Title: TOP Romantic Hotels in South Side, IL for 2025 - South Side Romantic Getaways | 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/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Romantic Hotels in South Side, IL ![](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 Romantic Hotels Tonight [24 Oct - 25 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [25 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635074842823&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next 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&travelerType=romantic) ## Top South Side Romantic Hotels ![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) ![Exterior](https://images.trvl-media.com/lodging/23000000/22360000/22355300/22355297/ffbe5574.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 (1001) "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/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites Downtown Chicago 9.0/10 Wonderful (3141) "Our stay was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce E £97 includes taxes & fees 16 Nov - 17 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.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) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Downtown Chicago 8.6/10 Excellent (2867) "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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.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) ### Warwick Allerton - Chicago Downtown Chicago 8.4/10 Very good (2925) "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) ![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) ![Hypo-allergenic bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.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 (2215) "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 £116 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, 1 King Bed, Lake View, Lakeside | Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e932b9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Congress Plaza Hotel Downtown Chicago 8.0/10 Very good (9570) "Area is great and walkable distance to touring areas. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro £83 includes taxes & fees 24 Nov - 25 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/eac67ea5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/340ea126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/f64fa789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/2c655ed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Millennium Knickerbocker Chicago Downtown Chicago 8.6/10 Excellent (1975) "Very good location, friendly staff and good breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria £105 includes taxes & fees 17 Nov - 18 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1faa6c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown River North Downtown Chicago 8.6/10 Excellent (5146) "Great place, good breakfast and the location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) NATIA £113 includes taxes & fees 16 Nov - 17 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/05f95ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast, lunch and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/b0f5bd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silversmith Hotel Chicago Downtown Downtown Chicago 9.4/10 Exceptional (2021) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl £123 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, al fresco dining, open daily](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/6dd4b8c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 2 Bedrooms, City View | City view](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/b54eb130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, al fresco dining, open daily](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/49502cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Virgin Hotels Chicago Downtown Chicago 9.2/10 Wonderful (1394) "Excellent hotel the rooms are awesome " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devita £207 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Virgin-Hotels-Chicago.h9119528.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=2025-11-07&endDate=2025-11-08®ionId=553248635074842823&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top South Side Hotel Reviews ![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." [](https://expedia.co.uk/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.Hotel-Information) ![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 "I stayed here for the Chicago marathon. It was cheaper than being closer to the start of the marathon. The staff was friendly and helpful. The property was clean. It is close to the 51st/53rd train station to be able to get to the expo at McCormick Place. Public transportation to the start of the marathon was also possible and easy. There was a Whole Foods close by. There were a few restaurants within 1 to 2 minutes outside of the door. I felt very safe walking around this area." [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) ![Chinatown Hotel Chicago](//images.trvl-media.com/lodging/2000000/1120000/1118400/1118357/85295fe8_y.jpg) ### Chinatown Hotel Chicago 10/10 Excellent "Lots of affordable parking in the area and right by the red line" [](https://expedia.co.uk/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ## 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) - 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