Title: Far Southeast Side Romantic Holidays 2025/2026 | 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 Romantic Holidays ## Book a Romantic Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 + Romantic 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 £771 per person 18 Dec - 23 Dec found 20 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) We loved the Pendry! Reviewed on 27 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-18/2025-12-23/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=Dhgv-z1bMfGmdYCS_63mycXzj8AHgEI_PGsBb_kpz7DRBtS78p6DLfPJ631ma7Mb) ![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 £1,331 per person 14 Dec - 19 Dec found 17 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home. Reviewed on 26 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-14/2025-12-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=b2aZMuH9dSEKApfdV5TobKoZlOk7wDMbfMyGIJ4xRFDYWJfOG18hrMdNk1sKV7S1) ![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 £1,495 per person 14 Dec - 19 Dec found 17 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,004 reviews) Beautiful place and service Reviewed on 29 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-14/2025-12-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=40&dealMarker=b2aZMuH9dSEKApfdV5TobKoZlOk7wDMbfMyGIJ4xRFAQA9AaalS6754FXm3cfCZT) ![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 £1,301 per person 14 Dec - 19 Dec found 17 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on 20 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-14/2025-12-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=b2aZMuH9dSEKApfdV5TobKoZlOk7wDMbfMyGIJ4xRFDk3gAy4-O3lakXrSgscFDp) ![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 £777 per person 18 Dec - 23 Dec found 20 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,248 reviews) Excellent stay. The hotel staff is very courteous and helpful, and the location is great! Reviewed on 28 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-18/2025-12-23/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=Dhgv-z1bMfGmdYCS_63mycXzj8AHgEI_PGsBb_kpz7CSjKhTnB-SaR33Y-DxdqIA) 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/2025-11-29/2025-12-06/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Far Southeast 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 £1,301 per person 14 Dec - 19 Dec found 17 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on 20 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-14/2025-12-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=b2aZMuH9dSEKApfdV5TobKoZlOk7wDMbfMyGIJ4xRFDk3gAy4-O3lakXrSgscFDp) ![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 £1,331 per person 14 Dec - 19 Dec found 17 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home. Reviewed on 26 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-14/2025-12-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=b2aZMuH9dSEKApfdV5TobKoZlOk7wDMbfMyGIJ4xRFDYWJfOG18hrMdNk1sKV7S1) ![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 £1,495 per person 14 Dec - 19 Dec found 17 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,004 reviews) Beautiful place and service Reviewed on 29 Oct 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-14/2025-12-19/?FromAirport=LHR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=b2aZMuH9dSEKApfdV5TobKoZlOk7wDMbfMyGIJ4xRFAQA9AaalS6754FXm3cfCZT) 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/2025-11-29/2025-12-06/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a romantic Far Southeast Side holiday #### How can I find the best Far Southeast Side vacation packages for couples? Use our easy-to-use holiday search tools to plan your most-romantic getaway to Far Southeast Side. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino. #### Can I book cheap Far Southeast Side romantic holidays for two? Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Far Southeast Side that start from £771. Prices and availability are subject to change. Additional terms may apply. #### What should I think about when booking a Far Southeast Side romantic getaway? The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure. #### What should I look for in a luxury romantic holiday to Far Southeast Side? Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service. #### Can I book a romantic hot-tub holiday in Far Southeast Side? What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter. #### How can I find romantic holidays for couples in Far Southeast Side that are all inclusive? Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available. #### Can I book a romantic trip to Far Southeast Side with free cancellation and/or flexible dates? Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print. #### Why should I book my Far Southeast Side romantic holiday with Expedia? At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing. ## 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) ### Top Romantic Holiday Destinations > - 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[Romantic Holidays in Venice](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179981/Venice) ## 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 ![QR code to download the app](data:image/png;base64,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)