Title: The 10 Best 5 Star Hotels in Far Southwest Side - 2025 Updated Prices | Expedia.co.uk [Far Southwest Side Travel Guide](https://expedia.co.uk/Far-Southwest-Side.dx553248635976475353)[Hotels in Far Southwest Side](https://expedia.co.uk/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Holiday Rentals in Far Southwest Side](https://expedia.co.uk/Far-Southwest-Side-Holiday-Rentals.d553248635976475353.Travel-Guide-HolidayRentals)[Flights to Far Southwest Side](https://expedia.co.uk/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Far-Southwest-Side.d553248635976475353.Car-Hire-Guide)[Far Southwest Side Holidays](https://expedia.co.uk/Far-Southwest-Side.d553248635976475353.Holidays-City-Breaks) ![](https://mediaim.expedia.com/destination/2/c1b10fc2dd618159f972d6db30c06f92.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Steve Luzzo # Compare and book 5 Star hotels in Far Southwest Side, Chicago ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Far Southwest Side 5 Star Hotels Tonight [8 Oct - 9 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475353&startDate=2025-10-08&endDate=2025-10-09&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [9 Oct - 10 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475353&startDate=2025-10-09&endDate=2025-10-10&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [10 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475353&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976475353&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Far 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) ![Gym](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4f5517f6.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) ![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 (1744) "Very accommodating and friendly staff, brilliant location" £377 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) ![Club Suite, 1 Bedroom, Lake View | 1 bedroom, hypo-allergenic bedding, down duvets, minibar](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/9a653c17.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) ![Mediterranean cuisine](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/71f6a2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Langham, Chicago Downtown Chicago 9.8/10 Exceptional (1006) "Great place to stay. " £475 includes taxes & fees 2 Nov - 3 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) ![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) ![Couples treatment room(s), body treatments, hydrotherapy, aromatherapy](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/6ca152e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Peninsula Chicago Downtown Chicago 9.8/10 Exceptional (1002) "Amazing hotel will be back for sure!" £568 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/fc796025.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 (1001) "Amazing hotel" £463 includes taxes & fees 2 Nov - 3 Nov [](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) ![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) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/cc9f9fd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/5001f31e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waldorf Astoria Chicago Downtown Chicago 9.4/10 Exceptional (1001) "Simply love this hotel" £502 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) ![Suite (LAKE MICHIGAN SUITE) | View from room](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/ef2f5d42.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/ca3d604d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Hyatt Chicago Downtown Chicago 9.6/10 Exceptional (1004) "beautiful room and hotel great bar!" £514 includes taxes & fees 3 Nov - 4 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) ![Interior entrance](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/8f021abe.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) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/37b7786f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nobu Hotel Chicago Downtown Chicago 9.4/10 Exceptional (732) "Great location, amenities and staff. " £357 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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/2fe2113a.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) ![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 (1002) "Beautiful place " £435 includes taxes & fees 7 Nov - 8 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) ![Indoor pool](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/w4000h2645x0y22-fdcb2993.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) ![Banquet hall](https://images.trvl-media.com/lodging/92000000/91140000/91139000/91138950/bd0f84f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The St. Regis Chicago Downtown Chicago 9.2/10 Wonderful (77) "Nice place " £561 includes taxes & fees 23 Oct - 24 Oct [](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) ![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) ![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) ### Art Villa West Town 10/10 Exceptional (2) " " £479 includes taxes & fees 13 Oct - 14 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-Far-Southwest-Side-Hotels.s50-0-d553248635976475353.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Far-Southwest-Side-Hotels.s50-0-d553248635976475353.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 Far 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 £147 5 Nov - 6 Nov includes taxes & fees 8.4/10 Very Good! (5,052 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 £156 31 Oct - 1 Nov includes taxes & fees 8.2/10 Very Good! (2,122 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 £122 29 Oct - 30 Oct includes taxes & fees 8.6/10 Excellent! (2,043 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 Far Southwest Side.](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F10%2F2025&endDate=10%2F10%2F2025®ionId=553248635976475353&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=09%2F10%2F2025&endDate=10%2F10%2F2025®ionId=553248635976475353&star=50&star=50&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F10%2F2025&endDate=10%2F10%2F2025®ionId=553248635976475353&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F10%2F2025&endDate=10%2F10%2F2025®ionId=553248635976475353&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F10%2F2025&endDate=10%2F10%2F2025®ionId=553248635976475353&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=09%2F10%2F2025&endDate=10%2F10%2F2025®ionId=553248635976475353&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 Far Southwest Side Venture to sights like Highland Community Bank and Dr. Percy Julian Residence as you discover Far Southwest Side. [See all hotels in Far Southwest Side](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23&adults=2®ionId=553248635976475353) ![](https://mediaim.expedia.com/destination/2/c1b10fc2dd618159f972d6db30c06f92.jpg?impolicy=fcrop&w=224&h=400&p=1&q=high) Photo by Steve Luzzo ## Top Far Southwest Side Hotel Reviews ## Find out more about Far Southwest Side ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - 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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[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) - [Greater Grand Crossing Hotels](https://www.expedia.co.uk/Greater-Grand-Crossing-Chicago-Hotels.0-n6132273-0.Travel-Guide-Filter-Hotels) - [Hometown Hotels](https://www.expedia.co.uk/Hometown-Hotels.d6132133.Travel-Guide-Hotels) - [Moxy Hotels in Hyde Park](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-MOXY.0-n117842-0--bMOXY.Travel-Guide-Filter-Hotels) - [Red Roof Inn Hotels in Hyde Park](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels-Red-Roof-Inn.0-n117842-0--bRedRoofInn.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) - [Hyde Park Hotels](https://www.expedia.co.uk/Hyde-Park-Chicago-Hotels.0-n117842-0.Travel-Guide-Filter-Hotels) - 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[Visit Morgan Park](https://www.expedia.co.uk/Chicago-Morgan-Park.dx6132289) - [Essex Holidays](https://www.expedia.co.uk/Essex.d6132371.Holidays-City-Breaks) - [Hyde Park Holidays](https://www.expedia.co.uk/Hyde-Park.d117842.Holidays-City-Breaks) - [Oak Lawn Holidays](https://www.expedia.co.uk/Oak-Lawn.d9227.Holidays-City-Breaks) - [Robie House](https://www.expedia.co.uk/Robie-House-Hyde-Park.d6064059.Attraction) - [Enterprise Rental Cars in Hyde Park](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Hyde-Park.d117842-c15.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Southwest Side](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Southwest-Side.d553248635976475403-c15.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in North Pullman](https://www.expedia.co.uk/Hertz-Car-Rentals-In-North-Pullman.d6132407-c40.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in Far Southeast Side](https://www.expedia.co.uk/Sixt-Car-Rentals-In-Far-Southeast-Side.d553248635976475411-c35.Car-Rental-Guide-Suppliers) - [Far Southeast Side Holiday Rentals](https://www.expedia.co.uk/Far-Southeast-Side-Holiday-Rentals.d553248635976475411.Travel-Guide-HolidayRentals) - [Hometown Holiday Rentals](https://www.expedia.co.uk/Hometown-Holiday-Rentals.d6132133.Travel-Guide-HolidayRentals) - [Oak Lawn Holiday Rentals](https://www.expedia.co.uk/Oak-Lawn-Holiday-Rentals.d9227.Travel-Guide-HolidayRentals) - [Book 5 Star Hotels in Far Southwest Side on Expedia.com](https://www.expedia.com/5Star-Far-Southwest-Side-Hotels.s50-0-d553248635976475353.Travel-Guide-Filter-Hotels)