Title: Book the Best ROMANTIC Hotels in South Side, IL - South Side Romantic Getaways | 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) ![](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__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 Romantic Hotels Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=553248635074842823&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/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 [Oct 24 - Oct 26](https://www.expedia.ca/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 [Oct 31 - Nov 2](https://www.expedia.ca/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](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 CA $263 CA $347 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.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) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/172457c3.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 CA $159 CA $187 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/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) ![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) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.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 CA $151 CA $177 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/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](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 (2926) "Nice hotel close to everything Enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $106 CA $166 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/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/58000000/57660000/57651200/57651125/2866aa1e.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) ![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 (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 CA $143 CA $216 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, City View | Living area](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/cc919354.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 CA $131 CA $154 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/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) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/2c655ed8.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) ### 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 CA $138 CA $195 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/896a6d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop 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) ### 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 CA $178 CA $209 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/c5cac7c3.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 CA $159 CA $230 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/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) ![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, alfresco 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) ![Rooftop bar, alfresco 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 CA $194 CA $276 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/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.ca/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 ![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.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.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." [](https://expedia.ca/Chicago-Hotels-Best-Western-Inn-Suites-Midway-Airport.h517495.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.ca/Chicago-Hotels-Chinatown-Hotel-Chicago.h1118357.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Cheap Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Cheap-Hotels.0-n6132245-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Family-Hotel.0-n6132245-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bronzeville](https://www.expedia.ca/Bronzeville-Chicago-Hotels-Luxury-Hotel.0-n6132245-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [B&B in Chicago 47th Street Station](https://www.expedia.ca/Chicago-47th-Street-Station-Bed-And-Breakfast.d6212783-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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