Title: TOP Luxury Hotels in Southwest Side, IL for 2026 - Southwest Side Upscale Hotels | 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 # Find luxury hotels in Southwest 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 Southwest Side Luxury Hotels Tonight [14 Dec - 15 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-12-14&endDate=2025-12-15&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [15 Dec - 16 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-12-15&endDate=2025-12-16&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-12-19&endDate=2025-12-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-12-26&endDate=2025-12-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Find out more about Southwest Side ### Southwest Sideand its attractions for luxury travelers In the Southwest Side of the United States, luxury travellers will discover a wealth of experiences that cater to both relaxation and adventure. Begin your journey at the stunning Red Rock Canyon National Conservation Area, where you can indulge in guided tours through striking sandstone formations and vibrant sunsets that paint the sky. For a taste of culture, visit the renowned Neon Museum, where the illuminated history of Las Vegas comes to life, offering a perfect backdrop for memorable family photos. Thrill-seekers will relish a day at the Las Vegas Strip, indulging in high-end shopping at designer boutiques and dining at Michelin-starred restaurants. Don't miss a chance to unwind at one of the luxurious spas in the area, like the Canyon Ranch SpaClub, known for its exceptional treatments and serene atmosphere. For comfortable accommodations, the upscale resorts near the Strip, such as The Venetian and Bellagio, provide an unparalleled experience with lavish rooms, exquisite pools, and attentive service. Staying in this area allows easy access to world-class entertainment options, ensuring a seamless blend of relaxation and excitement for the entire family. ## Top Southwest Side Hotel Reviews ![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 "The rooms are clean and well-maintained, and they’re conveniently located near a variety of shops." [](https://expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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 "The room view was beautiful! The staff was super attentive and helpful. " [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Everything was wonderful. We did not have breakfast" [](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "The service and how attentive everyone was definitely stood out to me." [](https://expedia.co.uk/Chicago-Hotels-River-Hotel.h2675313.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 "I would say this is the most convenient place to stay because everything is walking distance " [](https://expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.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 "Great place always. " [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg) ### Silversmith Hotel Chicago Downtown 10/10 Excellent "The staff is so friendly and helpful. We now have stayed here twice and enjoy the hotel. " [](https://expedia.co.uk/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Great hotel and staff. " [](https://expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg) ### Swissotel - Chicago 10/10 Excellent "The view from the room was nice. Loved the gym and amenities. A decent place to stay. The best part of the visit was the Palm restaurant (great food and service)." [](https://expedia.co.uk/Chicago-Hotels-Swissotel-Chicago.h17288.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) - [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) - [Hard Rock Hotels in Brighton Park ](https://www.expedia.co.uk/Brighton-Park-Chicago-Hotels-Hard-Rock-Hotels.0-n6132396-0--bHardRockHotels.Travel-Guide-Filter-Hotels) - [Brighton Park Hotels ](https://www.expedia.co.uk/Brighton-Park-Chicago-Hotels.0-n6132396-0.Travel-Guide-Filter-Hotels) - [Canaryville Hotels ](https://www.expedia.co.uk/Canaryville-Chicago-Hotels.0-n6132307-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Adults-Only-Resorts.0-0-d178248-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Beach-Hotels.0-0-d178248-tBeachHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Budget-Hotels.0-0-d178248-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Green Hotels in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Green-Sustainable.0-0-d178248-tGreenSustainable.Travel-Guide-Filter-Hotels) - [Historic Hotels in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Historic-Hotel.0-0-d178248-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with a View in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Hotel-With-A-View.0-0-d178248-thotelwithaview.Travel-Guide-Filter-Hotels) - [Hotels with Airport Transfers in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Hotel-With-Airport-Transfers.0-0-d178248-thotelwithairporttransfers.Travel-Guide-Filter-Hotels) - [Hotels with Breakfast in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Hotel-With-Breakfast.0-0-d178248-thotelwithbreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Parking in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Hotel-With-Parking.0-0-d178248-thotelwithparking.Travel-Guide-Filter-Hotels) - [Hotels with Indoor Pools in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Hotels-With-Indoor-Pools.0-0-d178248-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - [Hotels with Pool in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Hotels-With-Pool.0-0-d178248-tHotelswithPool.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Hotels-With-Waterslides.0-0-d178248-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Ski Hotels in Chicago ](https://www.expedia.co.uk/Chicago-Hotels-Ski-Hotels.0-0-d178248-tSkiHotels.Travel-Guide-Filter-Hotels) - [Chicago Hotels ](https://www.expedia.co.uk/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Gay-Friendly Hotels in Chicago Lawn ](https://www.expedia.co.uk/Chicago-Lawn-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132188-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Chicago Museum Campus ](https://www.expedia.co.uk/Chicago-Museum-Campus-Chicago-Hotels-Gay-Friendly-Hotel.0-n6175487-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Chinatown ](https://www.expedia.co.uk/Chinatown-Chicago-Hotels-Gay-Friendly-Hotel.0-n6003647-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Cicero ](https://www.expedia.co.uk/Cicero-Hotels-Gay-Friendly-Hotel.0-0-d89615-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Clearing ](https://www.expedia.co.uk/Clearing-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132083-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Dearborn Homes ](https://www.expedia.co.uk/Dearborn-Homes-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132366-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Englewood Hotels ](https://www.expedia.co.uk/Englewood-Chicago-Hotels.0-n101911-0.Travel-Guide-Filter-Hotels) - [Fuller Park Hotels ](https://www.expedia.co.uk/Fuller-Park-Chicago-Hotels.0-n6132374-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Gage Park ](https://www.expedia.co.uk/Gage-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132375-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gage Park Hotels ](https://www.expedia.co.uk/Gage-Park-Chicago-Hotels.0-n6132375-0.Travel-Guide-Filter-Hotels) - [Garfield Ridge Hotels ](https://www.expedia.co.uk/Garfield-Ridge-Chicago-Hotels.0-n6132357-0.Travel-Guide-Filter-Hotels) - [Business Hotels in Grand Boulevard ](https://www.expedia.co.uk/Grand-Boulevard-Chicago-Hotels-Business-Hotel.0-n6132310-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Hyde Park ](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Beach-Hotels.0-n117842-0-tBeachHotels.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Hyde Park ](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n117842-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Hyde Park ](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Golf-Hotels.0-n117842-0-tGolfHotels.Travel-Guide-Filter-Hotels) - [Hotels with Gym in Hyde Park ](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Hotel-With-Gym.0-n117842-0-thotelwithgym.Travel-Guide-Filter-Hotels) - [Hotels with Parking in Hyde Park ](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Hotel-With-Parking.0-n117842-0-thotelwithparking.Travel-Guide-Filter-Hotels) - [Lakeside Hotels in Hyde Park ](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Lakeside-Hotel.0-n117842-0-tlakesidehotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Hyde Park ](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Spa-Hotels.0-n117842-0-tSpaHotels.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Kenwood ](https://www.expedia.co.uk/Kenwood-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132343-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Mckinley Park Hotels ](https://www.expedia.co.uk/McKinley-Park-Chicago-Hotels.0-n6132389-0.Travel-Guide-Filter-Hotels) - [Hotels near Midway Intl. ](https://www.expedia.co.uk/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels) - [Casino Hotels in Near South Side ](https://www.expedia.co.uk/Near-South-Side-Chicago-Hotels-Casino-Hotel.0-n6132399-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Oak Lawn ](https://www.expedia.co.uk/Oak-Lawn-Hotels-Gay-Friendly-Hotel.0-0-d9227-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Princeton Park ](https://www.expedia.co.uk/Princeton-Park-Chicago-Hotels-Gay-Friendly-Hotel.0-n6132359-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Sleepy Hollow Hotels ](https://www.expedia.co.uk/Sleepy-Hollow-Chicago-Hotels.0-n6132427-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in South Side ](https://www.expedia.co.uk/South-Side-Hotels-Adults-Only-Resorts.0-0-d553248635074842823-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Hotels with Room Service in South Side ](https://www.expedia.co.uk/South-Side-Hotels-Hotel-With-Room-Service.0-0-d553248635074842823-thotelwithroomservice.Travel-Guide-Filter-Hotels) - [Hotels with Indoor Pools in South Side ](https://www.expedia.co.uk/South-Side-Hotels-Hotels-With-Indoor-Pools.0-0-d553248635074842823-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - [Washington Park Hotels ](https://www.expedia.co.uk/Washington-Park-Chicago-Hotels.0-n171466-0.Travel-Guide-Filter-Hotels) - [West Englewood Hotels ](https://www.expedia.co.uk/West-Englewood-Chicago-Hotels.0-n6132412-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in West Loop ](https://www.expedia.co.uk/West-Loop-Chicago-Hotels-Gay-Friendly-Hotel.0-n553248634029130868-0-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Flights to Chicago ](https://www.expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Delta Atlanta (ATL) to Chicago (MDW) flights ](https://www.expedia.co.uk/lp/flight-routes/delta-from-hartsfield-jackson-atlanta-intl-to-midway-intl/dl/atl/mdw) - [Delta Lagos (LOS) to Chicago (MDW) flights ](https://www.expedia.co.uk/lp/flight-routes/delta-from-murtala-muhammed-intl-to-midway-intl/dl/los/mdw) - [Klm London (LHR) to Chicago (MDW) flights ](https://www.expedia.co.uk/lp/flight-routes/klm-from-heathrow-to-midway-intl/kl/lhr/mdw) - [Porter Airlines Toronto (YTZ) to Chicago (MDW) flights ](https://www.expedia.co.uk/lp/flight-routes/porter-airlines-from-billy-bishop-toronto-city-to-midway-intl/pd/ytz/mdw) - [United Houston (IAH) to Chicago (MDW) flights ](https://www.expedia.co.uk/lp/flight-routes/united-from-george-bush-intercontinental-to-midway-intl/ua/iah/mdw) - [Virgin Atlantic London (LHR) to Chicago (MDW) flights ](https://www.expedia.co.uk/lp/flight-routes/virgin-atlantic-from-heathrow-to-midway-intl/vs/lhr/mdw) - [Flights from Albuquerque (ABQ) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/abq/mdw/albuquerque-to-chicago) - [Flights from Abu Dhabi (AUH) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/auh/mdw/abu-dhabi-to-chicago) - [Flights from Hartford (BDL) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/bdl/mdw/hartford-to-chicago) - [Flights from Bristol (BRS) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/brs/mdw/bristol-to-chicago) - [Flights from Burbank (BUR) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/bur/mdw/burbank-to-chicago) - [Flights from Baltimore (BWI) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/bwi/mdw/baltimore-to-chicago) - [Flights from Concord (CCR) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/ccr/mdw/concord-to-chicago) - [Flights from Charleston (CHS) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/chs/mdw/charleston-to-chicago) - [Flights from Champaign (CMI) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/cmi/mdw/champaign-to-chicago) - [Flights from Wenatchee (EAT) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/eat/mdw/wenatchee-to-chicago) - [Flights from Edinburgh (EDI) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/edi/mdw/edinburgh-to-chicago) - [Flights from Kalispell (FCA) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/fca/mdw/kalispell-to-chicago) - [Flights from Galesburg (GBG) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/gbg/mdw/galesburg-to-chicago) - [Flights from Glasgow (GLA) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/gla/mdw/glasgow-to-chicago) - [Flights from Geneva (GVA) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/gva/mdw/geneva-to-chicago) - [Flights from Hull (HUY) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/huy/mdw/hull-to-chicago) - [Flights from Washington (IAD) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/iad/mdw/washington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/ind/mdw/indianapolis-to-chicago) - [Flights from Iowa City (IOW) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/iow/mdw/iowa-city-to-chicago) - [Flights from New York (JFK) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/jfk/mdw/new-york-to-chicago) - [Flights from Kigali (KGL) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/kgl/mdw/kigali-to-chicago) - [Flights from London (LGW) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/lgw/mdw/london-to-chicago) - [Flights from London (LHR) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/lhr/mdw/london-to-chicago) - [Flights from Manchester (MAN) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/man/mdw/manchester-to-chicago) - [Flights from Kansas City (MCI) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/mci/mdw/kansas-city-to-chicago) - [Flights from Durham (MME) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/mme/mdw/durham-to-chicago) - [Flights from Norwich (NWI) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/nwi/mdw/norwich-to-chicago) - [Flights from Portland (PDX) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/pdx/mdw/portland-to-chicago) - [Flights from Phoenix (PHX) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/phx/mdw/phoenix-to-chicago) - [Flights from St. Cloud (STC) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/stc/mdw/st-cloud-to-chicago) - [Flights from Fayetteville (XNA) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/xna/mdw/fayetteville-to-chicago) - [Flights from Windsor (YQG) to Chicago (MDW) ](https://www.expedia.co.uk/lp/flights/yqg/mdw/windsor-to-chicago) - [Visit Brighton Park ](https://www.expedia.co.uk/Chicago-Brighton-Park.dx6132396) - [Visit Chicago Lawn ](https://www.expedia.co.uk/Chicago-Chicago-Lawn.dx6132188) - [Visit Gage Park ](https://www.expedia.co.uk/Chicago-Gage-Park.dx6132375) - [Visit West Elsdon ](https://www.expedia.co.uk/Chicago-West-Elsdon.dx6132410) - [S.s. 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 Luxury Hotels in Southwest Side on Expedia.com ](https://www.expedia.com/Southwest-Side-Hotels-Luxury-Hotel.0-0-d553248635976475403-tLuxuryHotel.Travel-Guide-Filter-Hotels)