Title: Far Southwest Side Mountain Holidays 2026/2026 | Expedia.co.uk ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southwest Side Mountain Holidays ## Book a Mountain Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Packages with flights are ATOL protected ## Top flight + Mountain hotel deals in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel £901 per person 14 Feb - 21 Feb found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area. Reviewed on 30 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-14/2026-02-21/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=14702161&paandie=true&HotelClass=40&dealMarker=P4c3tDm-3Z2RKFsG2Z3oQCmUbqPKRnK3DaaETLYd8U167_e6maW3IwCj1uny_fGc) ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago Save 100% on your flight £1,166 per person 6 Jan - 11 Jan found 12 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) The staff was amazing. Will be making a return stay. Reviewed on 30 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-06/2026-01-11/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=40&dealMarker=uSog25JsCb3HFkfGC2iWFHaNmdoi_7IG4nbzNNpYKXKD5c6OvyJrsAuE8UOS3I1y) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago £1,042 per person 6 Jan - 11 Jan found 12 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on 26 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-06/2026-01-11/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=9118CMhlUVus0nKenqud6fIGGjAVpUZPGo3XIcahj2q1BUSi86nCk1clLT4Td5mc) ![Fairmont Chicago at Millennium Park Gold Experience](https://images.trvl-media.com/lodging/65000000/64580000/64577200/64577141/2548c600_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Gold Experience Downtown Chicago £1,063 per person 14 Feb - 21 Feb found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (137 reviews) My wife and I really enjoyed our stay at this location. The accommodations were very nice. However, what really stuck out was the hotel staff, its the best that we have experienced. Reviewed on 5 Sept 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-14/2026-02-21/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=64577141&paandie=true&HotelClass=40&dealMarker=SN_Gb5bgYGob24PTijAnkNBnRAcU8dq4_q33fABlbTbQgwG1AWxS-wR4Ask6T_BH) ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago Save 100% on your flight £1,302 per person 17 Jan - 22 Jan found 17 hours ago Return flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on 29 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-17/2026-01-22/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=581213&paandie=true&HotelClass=40&dealMarker=uSog25JsCb3HFkfGC2iWFGP--Hhpn5mYmYmt_VkLxC9fqb1_HEwe9bt_jdLJBLQA) Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-02/2026-01-09/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago £1,042 per person 6 Jan - 11 Jan found 12 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on 26 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-06/2026-01-11/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=9118CMhlUVus0nKenqud6fIGGjAVpUZPGo3XIcahj2q1BUSi86nCk1clLT4Td5mc) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £1,065 per person 13 Jan - 20 Jan found 18 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful. Reviewed on 1 Dec 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-13/2026-01-20/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=uSog25JsCb3HFkfGC2iWFJzk9_tzeg-Kk0HLzosq8x6LoUe46AxQ9RyPKfo-QT9T) ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago Save 100% on your flight £1,166 per person 6 Jan - 11 Jan found 12 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) The staff was amazing. Will be making a return stay. Reviewed on 30 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-06/2026-01-11/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=uSog25JsCb3HFkfGC2iWFHaNmdoi_7IG4nbzNNpYKXKD5c6OvyJrsAuE8UOS3I1y) Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-02/2026-01-09/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![Chicago Marriott Suites O'Hare](https://images.trvl-media.com/lodging/1000000/10000/1500/1486/a5447791_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago Marriott Suites O'Hare £641 per person 26 Feb - 1 Mar found 1 day ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 8.8/10 Excellent! (1,002 reviews) Clean and comfy rooms. Reviewed on 27 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-26/2026-03-01/?FromAirport=EDI&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1486&paandie=true&HotelClass=40&dealMarker=1r-XD3dzByYrJ6IsYbPujTJRHv5ejVZODRaKYq-AYk2_su-M5ik29LxJ9YqPrrXV) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare £717 per person 26 Feb - 1 Mar found 1 day ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) a little pricey but convenient for traveling Reviewed on 2 Dec 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-26/2026-03-01/?FromAirport=EDI&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8058&paandie=true&HotelClass=40&dealMarker=1r-XD3dzByYrJ6IsYbPujZMnorPj-ZzIy7h0faFbtY0Hy9JEs16BFoqb4HxMBvXM) ![Hyatt Regency O'Hare Chicago](https://images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency O'Hare Chicago £671 per person 26 Feb - 1 Mar found 1 day ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 8.8/10 Excellent! (2,121 reviews) Easy access to airport Decent sized rooms with balconies on request. Would definitely recommend Reviewed on 1 Dec 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-26/2026-03-01/?FromAirport=EDI&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=5403&paandie=true&HotelClass=40&dealMarker=1r-XD3dzByYrJ6IsYbPujYYnj8gu9IPkW_rhbjwZGoEoQZ4tiMaJttXaW8B1pawn) Don't see what you're looking for? See all available trips from Edinburgh to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-02/2026-01-09/?FromAirport=EDI&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain holidays in Far Southwest Side Price found within the past 48 hours. Click for updated prices. ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £937 per person 3 Feb - 7 Feb found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on 26 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-03/2026-02-07/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=82RR9HJ6wOkvfh4nPUjG_OAfUN2seI1CXir4BAJhO2_UvNnwwCfdB_gapVa7oofF) ![Chicago luxury home suites](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/740de96f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago luxury home suites Downtown Chicago Save 100% on your flight £1,669 per person 3 Feb - 7 Feb found 1 day ago Return flight included London (LON) to Chicago (ORD) 10/10 Exceptional! (1 review) Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job. Reviewed on 26 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-03/2026-02-07/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=121424489&paandie=true&dealMarker=ZlTH4IFIh5H-5DiIuRl1qNSISTjaCs3SaevS0KX5sqkUnfUbU-nECleJ5nAnJMwR) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £971 per person 3 Feb - 7 Feb found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful. Reviewed on 1 Dec 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-03/2026-02-07/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=82RR9HJ6wOkvfh4nPUjG_C8S_6xpXcIFCQ5bRM8xT2cmK1_WL2fEKtR5o6gPOK4s) Don't see what you're looking for? See all available trips from London to Far Southwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-02/2026-01-09/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## More holidays you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## More Holiday Ideas [Flights to Far Southwest Side](https://expedia.co.uk/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Far Southwest Side Hotels](https://expedia.co.uk/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Far Southwest Side Holiday Rentals](https://expedia.co.uk/Far-Southwest-Side-Holiday-Rentals.d553248635976475353.Travel-Guide-HolidayRentals)[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) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)