Title: Book the Best ROMANTIC Hotels in Kenwood, Chicago from CA $178 - Kenwood Romantic Getaways | Expedia.ca [Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Kenwood Car Rentals](https://expedia.ca/Car-Rentals-In-Kenwood.d6132343.Car-Rental-Guide)[Kenwood Vacations](https://expedia.ca/Kenwood.d6132343.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/c96faeb4027380ae39b3c345c19d58bf.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Marc Jacobs # Find Romantic Hotels in Kenwood, Chicago from CA $178 ![](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 Kenwood Romantic Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6132343&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Kenwood Romantic Hotels ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.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) ### Warwick Allerton - Chicago Downtown Chicago 8.4/10 Very good (2933) "The lodging was super nice." CA $118 CA $180 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.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) ![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) ![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 8.8/10 Excellent (3120) "Our stay was great" CA $158 CA $186 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/15100/15087/f64fa789.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) ### Millennium Knickerbocker Chicago Downtown Chicago 8.6/10 Excellent (1996) "We have stayed here several times and love the hotel and location." CA $139 CA $196 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Chicago-Hotels-Millennium-Knickerbocker-Chicago.h15087.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/edcb7f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile Downtown Chicago 8.8/10 Excellent (3084) "Very nice location and everything was a 10/10" CA $152 CA $178 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/6ccd2813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, rooftop bar, cocktail bar](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/be0e472a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 King Bed, Accessible | Living room](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/72c3363f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago 9.4/10 Exceptional (3381) "Beautiful hotel! Would stay again " CA $233 CA $273 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.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) ![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) ![Standard Suite, 1 King Bed, Lake View, Lakeside](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e932b9a9.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) ### Congress Plaza Hotel Downtown Chicago 8.0/10 Very good (9438) "Beautiful hotel!" CA $179 CA $210 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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) ![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 cribs/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 (2868) "Had a great stay!" CA $194 CA $228 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.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) ### Palmer House a Hilton Hotel Downtown Chicago 8.4/10 Very good (2019) "Great place to stay." CA $258 CA $338 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/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) ![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) ![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](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chicago Downtown Chicago 9.4/10 Exceptional (3389) "Great place to stay " CA $327 CA $425 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.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) ![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/c5cac7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silversmith Hotel Chicago Downtown Downtown Chicago 9.4/10 Exceptional (2017) "Great place to stay " CA $182 CA $256 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.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=2025-10-30&endDate=2025-10-31®ionId=6132343&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Kenwood Hotel Reviews ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "I was there for the marathon and had a shared female room — the three others ended up being runners too, which was great. The location is fun and lively, but my room on the 9th floor was quiet. The staff were really nice — one of them even lent me his luck for the locker and gave me a card for the train. Very close to the start line. Amazing shopping and restaurants around. Loved it!" [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Perfect. Everything was great" [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Clean, quiet, safe!" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Just a good place to stay " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Nice and convenient place. Unique atmosphere " [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Crowne Plaza Chicago West Loop by IHG](//images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "Spent a night for our 14th anniversary. The staff was very thoughtful and kind. We appreciate the staff and room!" [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](//images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "This was perfect for Chicago Marathon. Good proximity to start and finish (about a mile) and was excellent location for spectating. " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "BEAUTIFUL IS ALL I HAVE TO SAY. THANKS SECURITY, I HAD A SAFE FUN FILLED DAY. LMAOOOO. Can't wait to return. " [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![River Hotel](//images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "Clean, comfortable room. Great view of the river. Great location. Staff was amazing. Great trip!" [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Kenwood? > If you and your partner need a romantic escape, we've got just the thing. Our guests also love Kenwood for its array of dining options and beautiful lakeside setting. If you'd like to explore some of the area's notable sights, you might make a stop by Lake Michigan, 4944 S Woodlawn Ave, or Obama's House. If you're interested in staying close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list. ### What is there to do in Kenwood? > There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Kenwood. Couples looking for a little of everything will enjoy Kenwood for its museums, restaurants, and lakeside setting. A visit to Lake Michigan, 4944 S Woodlawn Ave, or Obama's House might be just the ticket when you're checking out the sights. ## 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) - [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) - [Hotels near Chicago 47th Street Station](https://www.expedia.ca/Chicago-47th-Street-Station-Hotels.d6212783.Travel-Guide-Hotels) - [Guest Houses in Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Guest-Houses.d6212787-aaGuestHouses.Travel-Guide-Accommodation) - [Hotels near Chicago 51st-53rd Street Station](https://www.expedia.ca/Chicago-51st-53rd-Street-Station-Hotels.d6212787.Travel-Guide-Hotels) - 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[Grand Boulevard Hotels](https://www.expedia.ca/Grand-Boulevard-Chicago-Hotels.0-n6132310-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n117842-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Beach-Hotel.0-n117842-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Boutique-Hotel.0-n117842-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Cheap-Hotels.0-n117842-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Family-Hotel.0-n117842-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Historic-Hotel.0-n117842-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Hotel-With-Early-Check-In.0-n117842-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n117842-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Hotels-With-Kitchenettes.0-n117842-0-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hyatt Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Hyatt-Hotels.0-n117842-0--bHyattHotels.Travel-Guide-Filter-Hotels) - [La Quinta Inn & Suites Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-La-Quinta-Inn-Suites.0-n117842-0--bLaQuintaInnSuites.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Luxury-Hotel.0-n117842-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Oceanfront-Hotels.0-n117842-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Pet-Friendly-Hotel.0-n117842-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Hyde Park](https://www.expedia.ca/Hyde-Park-Chicago-Hotels-Spa-Hotel.0-n117842-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hyde Park Hotels](https://www.expedia.ca/Hyde-Park-Chicago-Hotels.0-n117842-0.Travel-Guide-Filter-Hotels) - [Hotels near Hyde Park Hair Salon](https://www.expedia.ca/Hyde-Park-Hair-Salon-Hotels.0-l553248621533116334-0.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Couples-Resorts-Hotels.0-n800025-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Magnificent Mile](https://www.expedia.ca/Magnificent-Mile-Chicago-Hotels-Romantic-Hotel.0-n800025-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - 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[Adults Only Resorts & in South Side](https://www.expedia.ca/South-Side-Hotels-Adults-Only-Resorts.0-0-d553248635074842823-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Boutique Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Boutique-Hotel.0-0-d553248635074842823-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Club Quarters Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Club-Quarters.0-0-d553248635074842823--bClubQuarters.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in South Side](https://www.expedia.ca/South-Side-Hotels-Hotel-With-Early-Check-In.0-0-d553248635074842823-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in South Side](https://www.expedia.ca/South-Side-Hotels-Hotels-With-Free-Parking.0-0-d553248635074842823-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in South Side](https://www.expedia.ca/South-Side-Hotels-Hotels-With-Smoking-Rooms.0-0-d553248635074842823-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-LGBT-Friendly-Hotel.0-0-d553248635074842823-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Loews Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Loews.0-0-d553248635074842823--bLoews.Travel-Guide-Filter-Hotels) - [Motel 6 Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Motel-6.0-0-d553248635074842823--bMotel6.Travel-Guide-Filter-Hotels) - [Sonesta Hotel in South Side](https://www.expedia.ca/South-Side-Hotels-Sonesta-Hotel.0-0-d553248635074842823--bSonestaHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in South Side](https://www.expedia.ca/South-Side-Hotels-Spa-Hotel.0-0-d553248635074842823-tSpaHotel.Travel-Guide-Filter-Hotels) - [South Side Hotels](https://www.expedia.ca/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels) - [Motels in South Side](https://www.expedia.ca/South-Side-Motels.d553248635074842823-aaMotels.Travel-Guide-Accommodation) - [Resorts in South Side](https://www.expedia.ca/South-Side-Resort-Hotels.d553248635074842823-aaResortHotels.Travel-Guide-Accommodation) - [Hotels with Early Check-in in The Loop](https://www.expedia.ca/The-Loop-Chicago-Hotels-Hotel-With-Early-Check-In.0-n800024-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels near University of Chicago](https://www.expedia.ca/University-Of-Chicago-Hotels.0-l6064081-0.Travel-Guide-Filter-Hotels) - [Hotels near University of Chicago Medicine](https://www.expedia.ca/University-Of-Chicago-Medicine-Hotels.0-l553248635389801569-0.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-All-Inclusive-Hotel.0-n171466-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Boutique-Hotel.0-n171466-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Cheap-Hotels.0-n171466-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Washington Park](https://www.expedia.ca/Washington-Park-Chicago-Hotels-Luxury-Hotel.0-n171466-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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[Hertz Rental Cars in Hyde Park](https://www.expedia.ca/Hertz-Car-Rentals-In-Hyde-Park.d117842-c40.Car-Rental-Guide-Suppliers) - [Book Hotels in Kenwood on Expedia.com](https://www.expedia.com/Kenwood-Chicago-Hotels-Romantic-Hotel.0-n6132343-0-tRomanticHotel.Travel-Guide-Filter-Hotels)