Title: Historic Route 66 Holidays 2026 from £1,065 | 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://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Historic Route 66 Holidays from £1,065 ## 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. ![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 £1,065 per person 26 Mar - 1 Apr found 2 hours 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 Save 100% on your flight £1,593 per person 6 Apr - 12 Apr found 3 hours ago Return direct flight included Manchester (MAN) 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 ![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 £1,736 per person 6 Apr - 12 Apr found 3 hours ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The staff and amenities Reviewed on 4 Feb 2026 ![Fairmont Chicago at Millennium Park Gold Experience](https://images.trvl-media.com/lodging/65000000/64580000/64577200/64577141/2548c600_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Gold Experience Downtown Chicago £1,329 per person 6 Apr - 12 Apr found 3 hours ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.2/10 Wonderful! (137 reviews) My wife and I really enjoyed our stay at this location. The accommodations were very nice. However, what really stuck out was the hotel staff, its the best that we have experienced. Reviewed on 5 Sept 2025 ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare £1,085 per person 26 Mar - 1 Apr found 2 hours ago Return direct flight included London (LHR) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay. Reviewed on 2 Feb 2026 ## 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 ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL Fully refundableReserve now, pay when you stay £76 5 Feb - 6 Feb includes taxes & fees 8/10 Very Good! (9,824 reviews) Good Reviewed on 30 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=702654640613646336) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Chicago - Magnificent Mile 300 E Ohio St Chicago IL Fully refundableReserve now, pay when you stay £79 11 Feb - 12 Feb includes taxes & fees 8.6/10 Excellent! (2,266 reviews) 2nd time at hotel and will come again. Reviewed on 28 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=21152&PinnedHotelID=21152&HadPinnedHotel=true®ionId=702654640613646336) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL Fully refundableReserve now, pay when you stay £140 21 Feb - 22 Feb includes taxes & fees 8.4/10 Very Good! (2,604 reviews) Great location and great hotel! Reviewed on 3 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=702654640613646336) [See all 19,954 properties in Historic Route 66](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F02%2F2026&endDate=06%2F02%2F2026®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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