Title: Far Southeast Side Mountain Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/829/b4cf8e95-0f92-4795-af28-19f97bbf7dad.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southeast 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 Southeast Side Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £567 per person 28 Feb - 3 Mar found 23 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Excellent location to stay in the heart of the city. Reviewed on 17 Dec 2025 ![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 £750 per person 28 Feb - 3 Mar found 23 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![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 £837 per person 28 Feb - 3 Mar found 23 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago £600 per person 28 Feb - 3 Mar found 23 hours ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Great amenities and staff Reviewed on 16 Dec 2025 ![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 £594 per person 28 Feb - 3 Mar found 23 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Love staying at the Emily. Very helpful friendly Staff & ccool architecture. Also love the front Patio in Summer☀️ Reviewed on 16 Dec 2025 Don't see what you're looking for? See all available trips from London to Far Southeast Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Mountain holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![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 £750 per person 28 Feb - 3 Mar found 23 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![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 £1,348 per person 29 Jan - 4 Feb found 1 day ago Return direct flight included Edinburgh (EDI) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 ![Four Seasons Hotel Chicago](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Seasons Hotel Chicago Downtown Chicago £1,504 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (999 reviews) Very nice amenities and wellness facility. High end shopping within a very short walk. Reviewed on 16 Dec 2025 Don't see what you're looking for? See all available trips from London to Far Southeast Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Mountain holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago £600 per person 28 Feb - 3 Mar found 23 hours ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Great amenities and staff Reviewed on 16 Dec 2025 ![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 £750 per person 28 Feb - 3 Mar found 23 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![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 £798 per person 3 Feb - 6 Feb found 2 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 Don't see what you're looking for? See all available trips from London to Far Southeast Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Mountain holidays in Far Southeast 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 £1,122 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Love staying at the Emily. Very helpful friendly Staff & ccool architecture. Also love the front Patio in Summer☀️ Reviewed on 16 Dec 2025 ![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 £1,364 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![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 £1,442 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 Don't see what you're looking for? See all available trips from London to Far Southeast Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-18/2026-01-25/?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 Southeast Side ](https://expedia.co.uk/Cheap-Flights-To-Far-Southeast-Side.d553248635976475411.Travel-Guide-Flights)[ Far Southeast Side Hotels ](https://expedia.co.uk/Far-Southeast-Side-Hotels.d553248635976475411.Travel-Guide-Hotels)[ Far Southeast Side Holiday Rentals ](https://expedia.co.uk/Far-Southeast-Side-Holiday-Rentals.d553248635976475411.Travel-Guide-HolidayRentals)[ Far Southeast Side Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Far-Southeast-Side.d553248635976475411.Car-Hire-Guide)[ Far Southeast Side Holidays ](https://expedia.co.uk/Far-Southeast-Side.d553248635976475411.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