Title: Historic Route 66 Holidays 2026 from £540 | Expedia.co.uk [Historic Route 66 Travel Guide](https://expedia.co.uk/Historic-Route-66.dx702654640613646336)[Hotels in Historic Route 66](https://expedia.co.uk/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[Holiday Rentals in Historic Route 66](https://expedia.co.uk/Historic-Route-66-Holiday-Rentals.d702654640613646336.Travel-Guide-HolidayRentals)[Flights to Historic Route 66](https://expedia.co.uk/Cheap-Flights-To-Historic-Route-66.d702654640613646336.Travel-Guide-Flights)[Historic Route 66 Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Historic-Route-66.d702654640613646336.Car-Hire-Guide) ![](https://images.trvl-media.com/place/553248621561870385/84ae69cd-06d7-48b8-a04a-f0221ac6efc7.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Historic Route 66 Holidays from £540 ## Book a 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 ### Your Historic Route 66 Holiday When adventure calls, answer it with a customised holiday package to Historic Route 66\. Wherever it is you're going and whatever your plans are, get set to discover a destination with so much to offer. Why not organise your trip to Historic Route 66 around a few of its most popular cities? [Virden](https://www.expedia.co.uk/Virden.d3000346639.Destination-Travel-Guides), [East Gillespie](https://www.expedia.co.uk/East-Gillespie.d553248634983261940.Destination-Travel-Guides) and [Gillespie](https://www.expedia.co.uk/Gillespie.d3000346284.Destination-Travel-Guides) all make great places to start. Whether you're planning to travel on a shoestring or in the lap of luxury, Expedia are here to help you organise your next dream Historic Route 66 holiday. ## Top Historic Route 66 Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago £540 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots. Reviewed on 18 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 1 day 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 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,007 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 ![Sandia Resort And Casino](https://images.trvl-media.com/lodging/2000000/1550000/1540100/1540099/06593b7d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sandia Resort And Casino Northeast Heights £1,449 per person 6 Feb - 13 Feb found 1 day ago Return flight included Manchester (MAN) to Albuquerque (ABQ) 9.4/10 Exceptional! (1,304 reviews) Very nice staff and beautiful clean room Reviewed on 11 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 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,382 reviews) Great amenities and staff Reviewed on 16 Dec 2025 ## Historic Route 66 Essential Information | Language | English | | ---------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Top Sights | [Arcadia Lake](https://www.expedia.co.uk/Arcadia-Lake-Oklahoma.d553248621532647455.Attraction) and [Flagstaff Convention and Visitors Bureau](https://www.expedia.co.uk/Flagstaff-Convention-And-Visitors-Bureau-Downtown-Flagstaff.d553248621561887573.Attraction) | ## Top hotels in Historic Route 66 ![Club Quarters Hotel, Central Loop, Chicago](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel, Central Loop, Chicago 111 West Adams Street Chicago IL Fully refundableReserve now, pay when you stay £67 19 Jan - 20 Jan 2026 includes taxes & fees 8.6/10 Excellent! (3,307 reviews) Good location, quiet room, comfy bed Reviewed on 13 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=19%2F01%2F2026&endDate=20%2F01%2F2026&selected=565746&PinnedHotelID=565746&HadPinnedHotel=true®ionId=702654640613646336) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL Fully refundableReserve now, pay when you stay £78 5 Jan - 6 Jan 2026 includes taxes & fees 8.8/10 Excellent! (3,498 reviews) Great location! Nice view, good staff Reviewed on 17 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=702654640613646336) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Silversmith Hotel Chicago Downtown 10 S Wabash Ave Chicago IL Fully refundableReserve now, pay when you stay £94 30 Dec - 31 Dec includes taxes & fees 9.2/10 Wonderful! (2,134 reviews) This hotel was great. In a perfect spot for walking the city and taking in all the sights. We had 3 of us in our group and we got the 1br with 2 queens beds and a pullout couch and it was perfect. The bar was fun and everyone we met in the staff were so friendly and helpful with suggestions on places ... Reviewed on 16 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=702654640613646336) [See all 19,642 properties in Historic Route 66](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F12%2F2025&endDate=21%2F12%2F2025®ionId=702654640613646336) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](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 holidays](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) ![Holiday in Month](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) ## Explore a world of travel with Expedia - 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