Title: Historic Route 66 Romantic Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/553248621561870385/84ae69cd-06d7-48b8-a04a-f0221ac6efc7.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Historic Route 66 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 Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Hotel Chicago Downtown, Autograph Collection by Marriott](https://images.trvl-media.com/lodging/1000000/130000/125400/125334/b72e1b95_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Chicago Downtown, Autograph Collection by Marriott Downtown Chicago £895 per person 24 Apr - 30 Apr found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (1,003 reviews) Hidden $50 “destination fee” billed to my credit card after I checked out, for nothing. Otherwise, great hotel. Reviewed on 30 Jan 2026 ![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 £1,611 per person 24 Apr - 30 Apr found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The amenities and staff are top tier!!! Reviewed on 1 Feb 2026 ![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 £1,116 per person 14 Mar - 21 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium. Reviewed on 31 Jan 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago £951 per person 7 Apr - 11 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean and nice room, fantastic breakfast. Nice iced vanilla latte from the 1st level bar area. About the only bad thing i can say was it would have been nice to know that after going in the room I had to insert my room key in the wall to have lights and power. Reviewed on 2 Feb 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago £1,030 per person 14 Mar - 21 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,229 reviews) Strong marijuana smell and stingy on amenities in the room Reviewed on 2 Feb 2026 Don't see what you're looking for? See all available trips from London to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-02/2026-03-09/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Historic Route 66 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 £1,036 per person 17 Mar - 20 Mar found 2 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on 24 Jan 2026 ![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 £1,611 per person 24 Apr - 30 Apr found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The amenities and staff are top tier!!! Reviewed on 1 Feb 2026 ![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 £1,905 per person 22 Apr - 26 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on 26 Jan 2026 Don't see what you're looking for? See all available trips from London to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-02/2026-03-09/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago £852 per person 17 Mar - 20 Mar found 2 hours ago Return flight included London (LON) to Chicago (ORD) 8.6/10 Excellent! (2,008 reviews) Staff was amazing throughout our stay. Room very clean, property well maintained. Great location Reviewed on 1 Feb 2026 ![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 £1,036 per person 17 Mar - 20 Mar found 2 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on 24 Jan 2026 ![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 £856 per person 17 Mar - 20 Mar found 2 hours ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Clean, nice amenities and great staff. Reviewed on 1 Feb 2026 Don't see what you're looking for? See all available trips from London to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-02/2026-03-09/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago £951 per person 7 Apr - 11 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean and nice room, fantastic breakfast. Nice iced vanilla latte from the 1st level bar area. About the only bad thing i can say was it would have been nice to know that after going in the room I had to insert my room key in the wall to have lights and power. Reviewed on 2 Feb 2026 ![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 £1,031 per person 7 Apr - 11 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again. Reviewed on 25 Jan 2026 ![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 £1,905 per person 22 Apr - 26 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on 26 Jan 2026 Don't see what you're looking for? See all available trips from London to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-02/2026-03-09/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a romantic Historic Route 66 holiday #### How can I find the best Historic Route 66 vacation packages for couples? Use our easy-to-use holiday search tools to plan your most-romantic getaway to Historic Route 66\. 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 Historic Route 66 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 Historic Route 66 that start from £852\. Prices and availability are subject to change. Additional terms may apply. #### What should I think about when booking a Historic Route 66 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 Historic Route 66? 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 Historic Route 66? 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 Historic Route 66 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 Historic Route 66 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 Historic Route 66 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 Historic Route 66 ](https://expedia.co.uk/Cheap-Flights-To-Historic-Route-66.d702654640613646336.Travel-Guide-Flights)[ Historic Route 66 Hotels ](https://expedia.co.uk/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[ Historic Route 66 Holiday Rentals ](https://expedia.co.uk/Historic-Route-66-Holiday-Rentals.d702654640613646336.Travel-Guide-HolidayRentals)[ Historic Route 66 Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Historic-Route-66.d702654640613646336.Car-Hire-Guide)[ Historic Route 66 Holidays ](https://expedia.co.uk/Historic-Route-66.d702654640613646336.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