Title: Historic Route 66 Beach Holidays 2026/2026 | 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 Beach Holidays ## Book a Beach 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 + Beach hotel deals in Historic Route 66 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 Save 100% on your flight £189 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on 22 Nov 2025 ![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 Save 100% on your flight £363 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on 26 Nov 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 £262 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 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 £228 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) 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 Don't see what you're looking for? See all available trips from Charlotte to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Beach holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 Save 100% on your flight £335 per person 27 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.6/10 Exceptional! (1,000 reviews) It is always an amazing place to stay Reviewed on 26 Nov 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 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 £545 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on 29 Nov 2025 Don't see what you're looking for? See all available trips from Charlotte to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Beach holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 £262 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on 3 Dec 2025 ![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 Save 100% on your flight £363 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on 26 Nov 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 Save 100% on your flight £383 per person 26 Feb - 1 Mar found 1 day ago Return flight included Charlotte (CLT) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) It's always perfection at the Trump. King suite with Lake view is the ultimate Reviewed on 2 Dec 2025 Don't see what you're looking for? See all available trips from Charlotte to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-05/2026-01-12/?FromAirport=CLT&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in Historic Route 66 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 £1,163 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on 26 Nov 2025 ![Chicago luxury home suites](https://images.trvl-media.com/lodging/122000000/121430000/121424500/121424489/740de96f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Chicago luxury home suites Downtown Chicago Save 100% on your flight £1,602 per person 13 Jan - 17 Jan found 9 hours ago Return direct flight included London (LON) to Chicago (ORD) 10/10 Exceptional! (1 review) Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job. Reviewed on 26 Nov 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 £1,187 per person 13 Jan - 17 Jan found 9 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on 29 Nov 2025 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/2026-01-05/2026-01-12/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find your perfect Historic Route 66 beach holiday #### How can I book the best beach holidays in Historic Route 66? Sometimes all you want is to kick back with the sun on your face and your toes in the sand. Plus-size the blissful on your Historic Route 66 beach holiday by checking out the best bays and using our neighbourhood filter to find accommodation nearby – or even with serene sea views. Use the reviews and our guest-rating filter to find the loveliest options. #### Can I book cheap beach holidays in Historic Route 66? For a budget beach break, consider staying a little further away from the sea, or choose self-catering rather than a hotel. You can use our amenities filter and map view to find the best cheap deals for you. Sunbathe for less with our affordable Historic Route 66 beach holidays, which start from £189\. Prices and availability are subject to change. Additional terms may apply. #### When can I go on a quiet beach holiday in Historic Route 66? Enjoy out-of-season seclusion on a beach holiday to Historic Route 66 during the quieter months. With fewer crowds competing for accommodation, you could bag a great deal, too. #### Why should I book family holidays in Historic Route 66 with beach access? If you have kids, beach holidays are more buckets and spades, lilos and sun cream than they are spa, cocktails and long reads – unless you book a holiday with beach access. It’s a family win. Even better, once the kids are in bed, you can sit on your bedroom balcony, listen to the waves and share a local tipple and stay in earshot of your sleeping beauties. #### How can I find a Historic Route 66 beachfront holiday? For the ultimate beach holiday, use our beachfront and sea view filters to whittle down your search results to find the perfect property, right on the water. #### How can I book last-minute Historic Route 66 beach holidays? Add a little spontaneity to your beach holiday by looking for a last-minute deal in Historic Route 66\. If you have set dates, pop them into the search and see what heaven awaits in just a few days. #### Can I find Historic Route 66 beach holidays which are all inclusive? A beach holiday to Historic Route 66 is one of the best occasions to treat yourself to an all-inclusive holiday package. Savour every sip of cocktail, every moment of sunshine, every blissful meal you didn’t have to cook yourself. And all included in the price. Just use our all-inclusive filter to see what’s available. #### Can I book a Historic Route 66 beach trip with free cancellation and/or flexible dates? Even if plans change, you don’t have to lose out. Use our filters to find accommodation with free cancellation, or even filter for buy now, pay later options. Once you’ve booked, log into your account to see all the details. #### Why should I book a Historic Route 66 beach holiday with Expedia? Our huge range of accommodation and flights mean you’ll find the best beach holidays in Historic Route 66 on Expedia in just a few clicks. It’s as easy as falling asleep to the sounds of the sea. ## 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 Beach Holiday Destinations > - [Beach Holidays in Croatia ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/43/Croatia) > - [Beach Holidays in Dunster ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/4363/Dunster) > - [Beach Holidays in England ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/11218/England) > - [Beach Holidays in Florida ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/211/Florida) > - [Beach Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/59/France) > - [Beach Holidays in Greece ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/67/Greece) > - [Beach Holidays in India ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/80/India) > - [Beach Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/86/Italy) > - [Beach Holidays in Morocco ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/122/Morocco) > - [Beach Holidays in Portugal ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/147/Portugal) > - [Beach Holidays in Sardinia ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/6048528/Sardinia) > - [Beach Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/11219/Scotland) > - [Beach Holidays in South Africa ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/165/South-Africa) > - [Beach Holidays in Spain ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/166/Spain) > - [Beach Holidays in Turkey ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/183/Turkey) > - [Beach Holidays in UK ](https://www.expedia.co.uk/lp/theme-holidays/beach-holidays/190/United-Kingdom) ## 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