Title: All Hotels by Destination Hotels in Southwest Side - 2025 Updated Prices | Expedia.co.uk [Southwest Side Travel Guide](https://expedia.co.uk/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.co.uk/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Holiday Rentals in Southwest Side](https://expedia.co.uk/Southwest-Side-Holiday-Rentals.d553248635976475403.Travel-Guide-HolidayRentals)[Flights to Southwest Side](https://expedia.co.uk/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Southwest Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southwest-Side.d553248635976475403.Car-Hire-Guide)[Southwest Side Holidays](https://expedia.co.uk/Southwest-Side.d553248635976475403.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) # Search Hotels by Destination Hotels in Southwest Side from £227 ![](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 prices for these dates Tonight [21 Oct - 22 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-21&endDate=2025-10-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [22 Oct - 23 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-22&endDate=2025-10-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [31 Oct - 2 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southwest Side Destination Hotels Hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/6b24bc12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/fae2da8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/d313af43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed (Founders) | Premium bedding, down duvets, pillow-top beds, minibar](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/18dae4e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Athletic Association, a Hyatt Hotel Downtown Chicago 9.0/10 Wonderful (1001) "Fantastic stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas £227 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Athletic-Association.h1118328.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=2025-11-04&endDate=2025-11-05®ionId=553248635976475403&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Hotels-Destination-Hotels.0-0-d553248635976475403--bDestinationHotels.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSouthwest-Side-Hotels-Destination-Hotels.0-0-d553248635976475403--bDestinationHotels.Travel-Guide-Filter-Hotels) ## Top Southwest Side Hotel Reviews ![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 "Parking was terrible and expensive. Recommend valet parking. Staff, very hard to talk to and i arrived at 3:30 scheduled to check in at 4 pm. Room wasn't available until 4;30. Staff wasn't to concerned." [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.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 "Nice location, rooms were nice size beds were comfortable water pressure was great " [](https://expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Location, location, location" [](https://expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.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 "The room was great, view gorgeous and all the hotel staff were welcoming and helpful! Location of the hotel is perfect to walk or take the metro. The restaurant had limited choices for breakfast but was nice enough and convenient." [](https://expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "It was affordable " [](https://expedia.co.uk/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "It was a beautiful property in a spectacular location. Close to transit, and walkable to everything in the loop. Would definitely stay again. " [](https://expedia.co.uk/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.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 "Excellent staff and overall experience. " [](https://expedia.co.uk/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Great Vibe!" [](https://expedia.co.uk/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "I like it" [](https://expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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) - [Benchmark Hotels in Austin](https://www.expedia.co.uk/Austin-Chicago-Hotels-Benchmark.0-n6132238-0--bBenchmark.Travel-Guide-Filter-Hotels) - 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Peter and Paul Church](https://www.expedia.co.uk/SS-Peter-And-Paul-Church-McKinley-Park.d6247219.Attraction) - [Rental cars Midway Intl. airport](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Midway-Intl.d5719117.Car-Hire-Guide) - [Book Destination Hotels in Southwest Side on Expedia.com](https://www.expedia.com/Southwest-Side-Hotels-Destination-Hotels.0-0-d553248635976475403--bDestinationHotels.Travel-Guide-Filter-Hotels)