Title: Historic Route 66 All inclusive 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 All inclusive Holidays ## Book a All inclusive 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 + All inclusive hotel deals in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wade Downtown Chicago £892 per person 27 Apr - 2 May found 6 hours ago Return direct flight included London (LGW) to Chicago (ORD) 8.4/10 Very Good! (1,444 reviews) I had a great stay at the Wade Hotel in Chicago! The room was very clean and comfortable, and the staff was friendly, professional, and welcoming from check-in to check-out. The amenities were convenient, and the location made it easy to get around the city. I would definitely stay here again and recommend it to anyone visiting Chicago. Reviewed on 9 Feb 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 £1,000 per person 27 Apr - 2 May found 6 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Friendly staff, tasteful room Reviewed on 11 Feb 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago £937 per person 27 Apr - 2 May found 6 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent. Reviewed on 9 Feb 2026 ![Virgin Hotels Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/63f8ab3d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Virgin Hotels Chicago Downtown Chicago £1,068 per person 27 Apr - 2 May found 6 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.2/10 Wonderful! (1,404 reviews) Great staff- very friendly Reviewed on 9 Feb 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 £1,080 per person 21 Apr - 28 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! 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/2026-03-11/2026-03-18/?FromAirport=LGW&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* All inclusive holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago £1,442 per person 7 Apr - 12 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Gorgeous property, facilities, and location. Reviewed on 6 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 £1,454 per person 7 Apr - 12 Apr found 1 day 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 ![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 £1,501 per person 7 Apr - 12 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) Everything was great… but the staff was absolutely amazing! Thank you for taking such great care of us. Reviewed on 24 Jan 2026 Don't see what you're looking for? See all available trips from Manchester to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-03-11/2026-03-18/?FromAirport=MAN&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night All inclusive 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 £790 per person 23 Mar - 26 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Friendly staff, tasteful room Reviewed on 11 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 £1,026 per person 23 Mar - 26 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on 3 Feb 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 £849 per person 23 Mar - 26 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! 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/2026-03-11/2026-03-18/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night All inclusive 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 £844 per person 16 Apr - 20 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Friendly staff, tasteful room Reviewed on 11 Feb 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago £889 per person 16 Apr - 20 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (3,392 reviews) Clean rooms, great reception, and beautiful views! Reviewed on 10 Feb 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 £894 per person 1 Apr - 5 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9/10 Wonderful! (380 reviews) My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone! 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/2026-03-11/2026-03-18/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All-inclusive Historic Route 66 holidays: everything you need to know #### Can I book Historic Route 66 all-inclusive holidays with airfare and meals? Use the all-inclusive filter to find amazing all-inclusive package holidays to Historic Route 66, then just add on your flights with a few simple clicks. With everything from cocktails to car hire booked in one go, all you need to decide is whether you’ll be sipping a mojito or a margarita at sunset. #### Why should I book a Historic Route 66 adults-only all-inclusive holiday? If screaming kids is your holiday nightmare, book a peaceful adults-only all-inclusive holiday to Historic Route 66 and you’re pretty much guaranteed a dreamy retreat. With those thoughtful grownup touches – beachside massage beds and live after-dinner music – an adults-only hotel levels up the sophistication on your holiday. #### Can I book last minute all-inclusive holidays to Historic Route 66? Last-minute breaks are a great way to find very cheap all-inclusive holidays to Historic Route 66\. If you can be flexible with your holiday dates, browse our best Historic Route 66 deals and use the all-inclusive filter to add everything that makes your hols perfect. #### Can I book a cheap all-inclusive Historic Route 66 trip? There are some nifty little tricks to find pocket-friendly all-inclusive breaks in Historic Route 66\. Try hunting around for cheaper deals in the off season by playing with your dates. Or you could also choose an all-inclusive hotel or resort a little off the beaten track. We have some top value deals starting at £790 – and they’re easy to find if you sort your results by price. Prices and availability are subject to change. Additional terms may apply. #### What should I look for when booking a 5-star all-inclusive holiday to Historic Route 66? All-inclusive holidays are such a treat, but a 5-star all-inclusive is a whole other level of luxury. Think butlers waiting on your every whim, infinity pools with epic ocean views and unlimited spa-ing for holiday heaven on cloud nine. #### What should I consider when booking a Historic Route 66 all-inclusive family holiday? If you’re holidaying with tots in tow, book an all-inclusive Historic Route 66 package with all the kid-friendly amenities. The action-packed kids’ clubs, the slide-tastic water parks, the fussy-eater-friendly restaurants: we have a stack of deals specifically designed with kids in mind. #### How can I find the best deals on all-inclusive holidays to Historic Route 66 in 2026/2027? There are great all-inclusive deals galore in Historic Route 66\. Sort by price to see the cheapest places to stay, and consider travelling during the less popular months when there’s often more availability and better prices. #### Can I book an all-inclusive Historic Route 66 package with free cancellation and/or flexible dates? Flexibility is key to a stress-free holiday. Look for properties with free cancellation or book now, pay later options. Then, if your plans change, just login to make changes in a few clicks. #### Why should I book an all-inclusive Historic Route 66 package holiday with Expedia? With a huge range of all-inclusive Historic Route 66 trips on offer, Expedia is your go-to place to find and book your trip. It’s super easy … and it’s all here. ## 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 All inclusive Holiday Destinations > - 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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