Title: The 10 Best 5 Star 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) # Compare and book 5 Star hotels in Southwest Side, Chicago ![](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 5 Star Hotels Tonight [13 Oct - 14 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-13&endDate=2025-10-14&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [14 Oct - 15 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475403&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southwest Side 5 Star Hotels ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Body treatments, body wraps, body scrubs, facials](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/743bf216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c35e7743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Trump International Hotel & Tower Chicago Downtown Chicago 9.4/10 Exceptional (1757) "Very accommodating and friendly staff, brilliant location" £379 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Trump-International-Hotel-Tower-Chicago.h1723215.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mediterranean cuisine](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/71f6a2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/0ab012f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/0c7c3240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Langham, Chicago Downtown Chicago 9.8/10 Exceptional (1008) "Great place to stay. " £478 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-The-Langham.h6309326.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/5616df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/acbf2aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago Downtown Chicago 9.8/10 Exceptional (1007) "Great weekend get away" £549 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Chicago-Hotels-The-Peninsula-Chicago.h581213.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/fc796025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/56d62feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/d00895ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Chicago Downtown Chicago 9.4/10 Exceptional (1007) "Amazing hotel" £466 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Four-Seasons-Hotel-Chicago.h25748.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/c47ab94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/cc9f9fd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/9baa79de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Chicago Downtown Chicago 9.4/10 Exceptional (1003) "Simply love this hotel" £475 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Waldorf-Astoria-Chicago.h2717582.Hotel-Information) ![Suite, Terrace (Water Tower) | 1 bedroom, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/ca3d604d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/3c600fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, al fresco dining ](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/6526f50f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Hyatt Chicago Downtown Chicago 9.6/10 Exceptional (1005) "beautiful room and hotel great bar!" £482 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Chicago-Hotels-Park-Hyatt-Chicago.h20695.Hotel-Information) ![Indoor pool, open 6:00 AM to 9:00 PM, pool loungers](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/486e1134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Designer toiletries, hair dryer, bathrobes, towels](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/ab9e9616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/82915bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/8f021abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobu Hotel Chicago Downtown Chicago 9.4/10 Exceptional (736) "Great location, amenities and staff. " £404 includes taxes & fees 30 Oct - 31 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Nobu-Hotel-Chicago.h36475533.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/30b68b68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Premium bedding, down duvets, pillow-top beds, minibar](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/bedaec25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/2fe2113a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/75bfc3f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Chicago Downtown Chicago 9.2/10 Wonderful (1003) "Greta stay " £439 includes taxes & fees 13 Nov - 14 Nov [](https://www.expedia.co.uk/Chicago-Hotels-The-Ritz-Carlton.h14447.Hotel-Information) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/0d225744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/bd0f84f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/5bfebb1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/43b7d4aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The St. Regis Chicago Downtown Chicago 9.2/10 Wonderful (77) "Nice place " £542 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Chicago-Hotels-The-St-Regis-Chicago.h91138950.Hotel-Information) ![Design Townhome, 3 Bedrooms, Kitchen, City View | Terrace/patio](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/93a33738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/3b336ff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/6cef91d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Townhome, 3 Bedrooms, Kitchen, City View | Living area | 55-inch Smart TV with digital channels, fireplace, Netflix](https://images.trvl-media.com/lodging/116000000/115170000/115163800/115163763/5df59d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Art Villa West Town 10/10 Exceptional (2) " " £715 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/Chicago-Hotels-Art-Villa.h115163763.Hotel-Information) ![](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%2F5Star-Southwest-Side-Hotels.s50-0-d553248635976475403.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Southwest-Side-Hotels.s50-0-d553248635976475403.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Southwest Side. ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St, Chicago, IL £134 9 Nov - 10 Nov includes taxes & fees 8.4/10 Very Good! (5,096 reviews) [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Chicago O'Hare Airport O'Hare International Airport, Chicago, IL £161 7 Nov - 8 Nov includes taxes & fees 8.2/10 Very Good! (2,132 reviews) [](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) ![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency O'Hare Chicago 9300 Bryn Mawr Ave, Rosemont, IL £123 26 Oct - 27 Oct includes taxes & fees 8.6/10 Excellent! (2,063 reviews) [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information) Still don't see what you're looking for? [See all properties in Southwest Side.](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976475403&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976475403&star=50&star=50&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976475403&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976475403&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976475403&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F10%2F2025&endDate=15%2F10%2F2025®ionId=553248635976475403&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Southwest Side Explore attractions like Balzekas Museum of Lithuanian Culture and Union Stock Yard Gate as you discover things to see and do in Southwest Side. [See all hotels in Southwest Side](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28&adults=2®ionId=553248635976475403) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495661-chicago-il-mdw-midway-intl.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) Photo by by Midway Intl Airport ## Top Southwest Side Hotel Reviews ## Find out more about Southwest Side ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - More ways to book - [1 Star Hotels in Chicago](https://www.expedia.co.uk/1Star-Chicago-Hotels.s10-0-d178248.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Chicago](https://www.expedia.co.uk/2Star-Chicago-Hotels.s20-0-d178248.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Northwest Side](https://www.expedia.co.uk/2Star-Northwest-Side-Hotels.s20-0-d553248635976475367.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Chicago](https://www.expedia.co.uk/3Star-Chicago-Hotels.s30-0-d178248.Travel-Guide-Filter-Hotels) - 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[5 Star Hotels in South Suburbs](https://www.expedia.co.uk/5Star-South-Suburbs-Hotels.s50-0-d6264251.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Western Suburbs](https://www.expedia.co.uk/5Star-Western-Suburbs-Hotels.s50-0-d6059325.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) - [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) - [Hotels near Chicago 35th Street-Lou Jones-Bronzeville Station](https://www.expedia.co.uk/Chicago-35th-Street-Lou-Jones-Bronzeville-Station-Hotels.d6213376.Travel-Guide-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) - [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) - [Little Village Hotels](https://www.expedia.co.uk/Little-Village-Chicago-Hotels.0-n6132436-0.Travel-Guide-Filter-Hotels) - [Lower West Side Hotels](https://www.expedia.co.uk/Lower-West-Side-Chicago-Hotels.0-n6132386-0.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) - [Sleepy Hollow Hotels](https://www.expedia.co.uk/Sleepy-Hollow-Chicago-Hotels.0-n6132427-0.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) - [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) - 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