Title: Great River Road Romantic Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/7956/10192ec4-1419-451d-9e2e-50909ca12beb.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Great River Road Romantic Holidays ## Book a Romantic 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 + Romantic hotel deals in Great River Road Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago £642 per person 1 Mar - 8 Mar found 21 hours ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on 8 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 £1,162 per person 1 Mar - 8 Mar found 22 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on 14 Dec 2025 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago Save 100% on your flight £784 per person 1 Mar - 8 Mar found 21 hours ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Great location, clean room and friendly staff! Reviewed on 14 Dec 2025 ![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 Save 100% on your flight £803 per person 1 Mar - 8 Mar found 21 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on 4 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 £1,332 per person 1 Mar - 8 Mar found 21 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!! Reviewed on 15 Dec 2025 Don't see what you're looking for? See all available trips from London to Great River Road [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=LON&Destination=MSP&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Great River Road Price found within the past 48 hours. Click for updated prices. ![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 £875 per person 1 Feb - 5 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on 3 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 £1,162 per person 1 Mar - 8 Mar found 22 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on 14 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 £1,332 per person 1 Mar - 8 Mar found 21 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!! Reviewed on 15 Dec 2025 Don't see what you're looking for? See all available trips from London to Great River Road [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=LON&Destination=MSP&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Great River Road 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 £773 per person 1 Feb - 5 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on 14 Dec 2025 ![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 £875 per person 1 Feb - 5 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on 3 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 £913 per person 1 Feb - 5 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived. Outstanding!! Reviewed on 15 Dec 2025 Don't see what you're looking for? See all available trips from London to Great River Road [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=LON&Destination=MSP&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a romantic Great River Road holiday #### How can I find the best Great River Road vacation packages for couples? Use our easy-to-use holiday search tools to plan your most-romantic getaway to Great River Road. 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 Great River Road 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 Great River Road that start from £642\. Prices and availability are subject to change. Additional terms may apply. #### What should I think about when booking a Great River Road 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 Great River Road? 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 Great River Road? 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 Great River Road 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 Great River Road 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 Great River Road 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 > - [Romantic Holidays in Barcelona ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179992/Barcelona) > - [Romantic Holidays in Cornwall ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/10558/Cornwall) > - [Romantic Holidays in Cyprus ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/45/Cyprus) > - [Romantic Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/59/France) > - [Romantic Holidays in Greece ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/67/Greece) > - [Romantic Holidays in Ibiza ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/1559/Ibiza-Town) > - [Romantic Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/86/Italy) > - [Romantic Holidays in Morocco ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/122/Morocco) > - [Romantic Holidays in Paris ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179898/Paris) > - [Romantic Holidays in Portugal ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/147/Portugal) > - [Romantic Holidays in Rome ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179899/Rome) > - [Romantic Holidays in Santorini ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/177970/Santorini) > - [Romantic Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/11219/Scotland) > - [Romantic Holidays in Thailand ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/178/Thailand) > - [Romantic Holidays in the Maldives ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/109/Maldives) > - [Romantic Holidays in the United Kingdom ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/190/United-Kingdom) > - [Romantic Holidays in the USA ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/201/United-States-Of-America) > - [Romantic Holidays in Turkey ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/183/Turkey) > - [Romantic Holidays in Venice ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179981/Venice) ## More Holiday Ideas [Flights to Great River Road ](https://expedia.co.uk/Cheap-Flights-To-Great-River-Road.d702655377080487936.Travel-Guide-Flights)[ Great River Road Hotels ](https://expedia.co.uk/Great-River-Road-Hotels.d702655377080487936.Travel-Guide-Hotels)[ Great River Road Holiday Rentals ](https://expedia.co.uk/Great-River-Road-Holiday-Rentals.d702655377080487936.Travel-Guide-HolidayRentals)[ Great River Road Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Great-River-Road.d702655377080487936.Car-Hire-Guide)[ Great River Road Holidays ](https://expedia.co.uk/Great-River-Road.d702655377080487936.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