Title: Beach Vacations in Historic Route 66 2026 | Expedia.ca ![](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 Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 Plan, book, and manage your trip all in one place ## Flight and Beach hotel deals in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston CA $547 per person Mar 12 - Mar 15 found 16 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) I would stay here again if I need to stay in Evanston again. Thanks Reviewed on Jan 19, 2026 ![The Inn at Vanessie](https://images.trvl-media.com/lodging/1000000/90000/85300/85222/181de913_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Vanessie Downtown Santa Fe CA $1,154 per person Apr 7 - Apr 14 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Albuquerque (ABQ) 8.8/10 Excellent! (1,001 reviews) Always fun to stay in a different room at The Vanessie. The staff is super friendly and rooms are nicely finished. The breakfast menu is always delicious and the cook is cheerful with a nice smile. We love staying there on our way to AZ. Highly recommend!! Reviewed on Jan 12, 2026 ![Hotel Santa Fe](https://images.trvl-media.com/lodging/1000000/20000/19400/19360/1968861c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Santa Fe Downtown Santa Fe CA $1,360 per person Apr 7 - Apr 14 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Albuquerque (ABQ) 9.2/10 Wonderful! (1,055 reviews) My husband ordered a breakfast but the muffin wasn’t Reviewed on Jan 20, 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 CA $929 per person Mar 5 - Mar 7 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on Jan 20, 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 CA $809 per person Feb 25 - Mar 1 found 17 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 Don't see what you're looking for? See all available trips from Columbus to Historic Route 66 [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&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. ![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 CA $929 per person Mar 5 - Mar 7 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on Jan 20, 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 CA $2,211 per person Mar 25 - Apr 1 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on Jan 20, 2026 ![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 CA $1,052 per person Mar 13 - Mar 15 found 13 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Yes didn’t know you get free breakfast Reviewed on Jan 4, 2026 Don't see what you're looking for? See all available trips from Columbus to Historic Route 66 [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&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. ![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 CA $753 per person Apr 10 - Apr 13 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85\. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though. Reviewed on Jan 22, 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 CA $1,394 per person Apr 3 - Apr 6 found 15 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on Jan 20, 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 CA $876 per person Apr 10 - Apr 13 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on Jan 8, 2026 Don't see what you're looking for? See all available trips from Columbus to Historic Route 66 [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&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. ![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 CA $715 per person Apr 13 - Apr 17 found 17 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85\. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though. Reviewed on Jan 22, 2026 ![The Wildwood Hotel](https://images.trvl-media.com/lodging/2000000/1770000/1768200/1768149/800a6847_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wildwood Hotel CA $1,002 per person Mar 18 - Mar 22 found 1 day ago Roundtrip flight included Toronto (YYZ) to St. Louis (STL) 9.2/10 Wonderful! (1,600 reviews) Room was clean and big with a separate sitting area. We would definitely stay there again . Reviewed on Jan 21, 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 CA $875 per person Apr 13 - Apr 17 found 17 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on Jan 18, 2026 Don't see what you're looking for? See all available trips from Columbus to Historic Route 66 [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in Historic Route 66 #### What are some benefits when booking beach vacations in Historic Route 66? When you travel to the beach in Historic Route 66, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. #### How can I book the best beach vacations in Historic Route 66? To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Historic Route 66 trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. #### Can I book cheap beach vacations in Historic Route 66? There are quite a few things you can do to get cheap beach vacations in Historic Route 66\. Prices range from CA $547, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. #### Can I book beach packages? Yes, and you'll find quite a few beach packages available in Historic Route 66\. These package deals let you save by booking your accommodation and your flight together with savings of up to 22\. #### Why should I book family beach vacations? When you're travelling with the family to Historic Route 66, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. #### How can I find a beachfront vacation in Historic Route 66? It's easy to find a beachfront vacation accommodation in Historic Route 66 using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline. #### How can I book last-minute beach vacations? Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Historic Route 66 as your destination and see what's available. #### Can I find all-inclusive beach vacations ? Yes, all you have to do to find all-inclusive beach vacations in Historic Route 66 is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. #### Can I book a beach trip that's fully refundable? Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout United States of America. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too. #### Why should I book beach vacations with Expedia? When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips. ## More vacations 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 Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Beach Vacation Destinations > - [Myrtle beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/601685/Myrtle-Beach) > - [Miami beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8833/Miami-Beach) > - [Florida beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/211/Florida) > - [Barbados beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/16/Barbados) > - [South beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6138745/South-Beach) > - [Palm beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/9061/Palm-Beach) > - [Daytona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023995/Daytona-Beach) > - [Newport beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8111/Newport-Beach) > - [Vero beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023660/Vero-Beach) > - [India beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/80/India) > - [Laguna beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6298668/Laguna-Beach) > - [Ontario beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/2680/Ontario) > - [Canada beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/31/Canada) > - [Barcelona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/179992/Barcelona) > - [Fort Myers beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/7194/Fort-Myers-Beach) > - [Portugal beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/147/Portugal) > - [Italy beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/86/Italy) > - [Thailand beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/178/Thailand) > - [France beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/59/France) ## More Vacations Ideas [Flights to Historic Route 66 ](https://expedia.ca/Cheap-Flights-To-Historic-Route-66.d702654640613646336.Travel-Guide-Flights)[ Historic Route 66 Hotels ](https://expedia.ca/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[ Historic Route 66 Vacation Rentals ](https://expedia.ca/Historic-Route-66-Vacation-Rentals.d702654640613646336.Travel-Guide-VacationRentals)[ Historic Route 66 Car Rentals ](https://expedia.ca/Car-Rentals-In-Historic-Route-66.d702654640613646336.Car-Rental-Guide)[ Historic Route 66 Vacations ](https://expedia.ca/Historic-Route-66.d702654640613646336.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on 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