Title: Romantic 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 Romantic 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 Romantic hotel deals 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 $898 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Staff was extremely polite, rooms were clean. No issues at all Reviewed on Feb 2, 2026 ![Rosewood Inn of the Anasazi](https://images.trvl-media.com/lodging/1000000/10000/2200/2125/f0a7407b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Rosewood Inn of the Anasazi Downtown Santa Fe CA $2,774 per person Mar 15 - Mar 22 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Albuquerque (ABQ) 9.4/10 Exceptional! (851 reviews) I can't rave enough about my stay! From the welcoming staff and manger to the beautiful room. Everything was perfection - rooms are well appointed and includes a lovely turn down service nightly. Food and lobby bar are always busy- great tequila cocktails! Hotel provides car service within 3 miles - saving you from uber-while riding in style. This is a 5 star hotel and 5 stars to the staff for making my birthday stay amazing and unforgettable! Reviewed on Feb 2, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $967 per person Mar 14 - Mar 18 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. 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 $1,605 per person Mar 15 - Mar 22 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Albuquerque (ABQ) 8.8/10 Excellent! (1,001 reviews) The staff was amazing, literally took us to our room and showed us around ! Then we ordered door dash and they delivered it to the front desk and instead of calling for us to come grab it, he brought it to our room! Talk about impressed ! Went above and beyond ! Reviewed on Jan 26, 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 $1,216 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) 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 Jan 26, 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/2026-03-04/2026-03-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 $1,216 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) 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 Jan 26, 2026 ![Rosewood Inn of the Anasazi](https://images.trvl-media.com/lodging/1000000/10000/2200/2125/f0a7407b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Rosewood Inn of the Anasazi Downtown Santa Fe CA $2,774 per person Mar 15 - Mar 22 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Albuquerque (ABQ) 9.4/10 Exceptional! (851 reviews) I can't rave enough about my stay! From the welcoming staff and manger to the beautiful room. Everything was perfection - rooms are well appointed and includes a lovely turn down service nightly. Food and lobby bar are always busy- great tequila cocktails! Hotel provides car service within 3 miles - saving you from uber-while riding in style. This is a 5 star hotel and 5 stars to the staff for making my birthday stay amazing and unforgettable! Reviewed on Feb 2, 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 $1,384 per person Mar 15 - Mar 19 found 6 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on Feb 3, 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/2026-03-04/2026-03-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $693 per person Apr 2 - Apr 5 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on Jan 19, 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 $1,216 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) 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 Jan 26, 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 CA $783 per person Apr 3 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Staff was extremely polite, rooms were clean. No issues at all Reviewed on Feb 2, 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/2026-03-04/2026-03-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic 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 $898 per person Apr 2 - Apr 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Staff was extremely polite, rooms were clean. No issues at all Reviewed on Feb 2, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $967 per person Mar 14 - Mar 18 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on Jan 19, 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 $1,384 per person Mar 15 - Mar 19 found 6 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on Feb 3, 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/2026-03-04/2026-03-11/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Historic Route 66 vacations #### What are some of the benefits of booking a romantic Historic Route 66 vacation? When booking a romantic Historic Route 66 vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in United States of America. #### How can I find the best vacation packages for couples? If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the Historic Route 66 destination, and you'll be met with an array of options for you and your partner to enjoy. #### Can I find cheap romantic vacations for 2 in Historic Route 66? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $693 and can enjoy savings of up to 31 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first. #### What do I need to consider when booking a romantic getaway in Historic Route 66? Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout Historic Route 66 certainly come in handy here. #### What amenities should I look for in a luxury romantic vacation? If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to Historic Route 66. #### Can I book a romantic Historic Route 66 vacation with a hot tub? Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them. #### How can I find romantic vacation getaways that are all-inclusive? An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your Historic Route 66 search. #### Can I book a romantic trip to Historic Route 66 that is fully refundable? Several romantic Historic Route 66 vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements. #### Why should I book a romantic vacation with Expedia? Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage. ## 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 Romantic Vacation Destinations > - [Romantic vacations in Toronto ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178314/Toronto) > - [Romantic vacations in Nova Scotia ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11173/Nova-Scotia) > - [Romantic vacations in Montreal ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178288/Montreal) > - [Romantic vacations in Vancouver ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178315/Vancouver) > - [Romantic vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180017/Quebec) > - [Romantic vacations in the Niagara Falls ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/602721/Niagara-Falls) > - [Romantic vacations in Alberta ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11111/Alberta) > - [Romantic vacations in Victoria ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/1418/Victoria) > - [Romantic vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/8028/Jasper) > - [Romantic vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4332/Banff) > - [Romantic vacations in Ottawa ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178296/Ottawa) > - [Romantic vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/55374/Mont-Tremblant) > - [Romantic vacations in Kingston ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180034/Kingston) > - [Romantic vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4115/Whistler) > - [Romantic vacations in Winnipeg ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6141041/Winnipeg) > - [Romantic vacations in Muskoka ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6343146/Muskoka-District) > - [Romantic vacations in Collingwood ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11938/Collingwood) > - [Romantic vacations in Calgary ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178245/Calgary) > - [Romantic vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/31/Canada) ## 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