Title: All Hotels by Destination Hotels in Southwest Side - 2026 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) ![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by by Midway Intl Airport # Search Hotels by Destination Hotels in Southwest Side from £122 - ![](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 [19 Dec - 20 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [20 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-12-20&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southwest Side Destination Hotels ![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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/4c4241f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/56ac30bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/2000000/1120000/1118400/1118328/392edec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chicago Athletic Association, a Hyatt Hotel [](https://www.expedia.co.uk/Chicago-Hotels-Chicago-Athletic-Association.h1118328.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1001) "It’s amazing historical property " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joel £122 includes taxes & fees 4 Jan - 5 Jan 2026 [](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=2026-01-03&endDate=2026-01-04®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 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Amazing experience! The rooms were spotless, comfortable, and thoughtfully maintained. All hotel amenities were clean, well-organized, and ready to use. The breakfast was excellent, with a great variety of options to choose from. What truly made this stay extraordinary was the outstanding service. Brad, Vicente, Cruz, Eric, Ruby, and the entire team went above and beyond to ensure a memorable experience. Their professionalism, kindness, and attention to detail were exceptional. Without a doubt, this was a unique and unforgettable stay — truly a hotel that exceeds five-star expectations. ❤️" [](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg) ### Swissotel - Chicago 10/10 Excellent "Wonderful. It’s just an overnight stay but the staff is exceptional " [](https://expedia.co.uk/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Nice size clean and Cozy room. Great staff. Great food at all the restaurants. " [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "free alc beverages at night, huge breakfast " [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Great location, very clean room!" [](https://expedia.co.uk/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "The staff was very friendly and helpful. Anyth" [](https://expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg) ### LondonHouse Chicago, Curio Collection by Hilton 10/10 Excellent "Clean room, beautiful hotel, location is great walking distance to everything. My only complaint was the pillows but that’s just an opinion. I’d stay here again!" [](https://expedia.co.uk/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Great location! Nice view, good staff " [](https://expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg) ### Crowne Plaza Chicago West Loop by IHG 10/10 Excellent "Friendly/Helpful staff made for a great welcome! " [](https://expedia.co.uk/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.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) - [Bridgeport Hotels ](https://www.expedia.co.uk/Bridgeport-Chicago-Hotels.0-n6132075-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Brighton Park ](https://www.expedia.co.uk/Brighton-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132396-0-tGayFriendlyHotel.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)