Title: Pet-friendly 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 Pet-friendly 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 Pet-friendly 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 $817 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Best breakfast buffet I’ve ever had while in Chicago. ALL staff was nice, welcoming and willing to be of assistance. Definitely plan on staying again the next time I’m in Chicago‼️ Reviewed on Mar 29, 2026 ![The Hacienda & Spa at Hotel Santa Fe](https://images.trvl-media.com/lodging/1000000/810000/802700/802697/c5bd86f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hacienda & Spa at Hotel Santa Fe Downtown Santa Fe CA $2,440 per person May 6 - May 13 found 1 hour ago Roundtrip non-stop flight included Toronto (YTO) to Albuquerque (ABQ) 9.4/10 Exceptional! (1,006 reviews) This was our best stay on a two month road trip. I can’t say enough how much we enjoyed this hotel and would give it six stars if I could. The facilities were excellent including a spacious room with a patio. What really made it special was the exceptionably friendly and helpful staff. Special thanks to Soriano for her help and friendly smile. We loved the evening happy hour, especially when it was on the upper patio. Reviewed on Mar 25, 2026 ![Hotel Santa Fe](https://images.trvl-media.com/lodging/1000000/20000/19400/19360/e12ea3f0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Santa Fe Downtown Santa Fe CA $2,364 per person May 6 - May 13 found 1 hour ago Roundtrip non-stop flight included Toronto (YTO) to Albuquerque (ABQ) 9.2/10 Wonderful! (1,108 reviews) Great location. Clean room. Reviewed on Mar 28, 2026 ![The Inn at Vanessie](https://images.trvl-media.com/lodging/1000000/90000/85300/85222/84270b87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Vanessie Downtown Santa Fe CA $1,552 per person May 6 - May 13 found 1 hour ago Roundtrip non-stop flight included Toronto (YTO) to Albuquerque (ABQ) 8.8/10 Excellent! (1,005 reviews) Great stay! Good location near the Plaza, friendly staff, clean, comfortable rooms, and a great complimentary breakfast. Would definitely stay here again! Reviewed on Mar 21, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,109 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Thank you for your exceptional hospitality Reviewed on Mar 29, 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Pet-friendly 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/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,109 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Thank you for your exceptional hospitality Reviewed on Mar 29, 2026 ![Bishop's Lodge, Auberge Collection](https://images.trvl-media.com/lodging/1000000/50000/40800/40737/4b0bf4d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bishop's Lodge, Auberge Collection Tesuque CA $5,325 per person May 6 - May 13 found 1 hour ago Roundtrip non-stop flight included Toronto (YTO) to Albuquerque (ABQ) 9.4/10 Exceptional! (99 reviews) Check whether everything in the room actually works before guests check-in. Reviewed on Mar 23, 2026 ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/29a217ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago CA $1,418 per person May 8 - May 11 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,001 reviews) The pool was a little tight and dated. The spa overall felt a little dated. The fitness area was fabulous. Reviewed on Mar 22, 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Pet-friendly 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 $802 per person May 19 - May 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Best breakfast buffet I’ve ever had while in Chicago. ALL staff was nice, welcoming and willing to be of assistance. Definitely plan on staying again the next time I’m in Chicago‼️ Reviewed on Mar 29, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,177 per person Jun 19 - Jun 22 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Amazing experience will be back soon Reviewed on Mar 29, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,178 per person Jun 20 - Jun 23 found 2 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Pet-friendly holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![The Inn at Vanessie](https://images.trvl-media.com/lodging/1000000/90000/85300/85222/84270b87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Vanessie Downtown Santa Fe CA $1,217 per person Jun 15 - Jun 19 found 20 hours ago Roundtrip non-stop flight included Toronto (YTO) to Albuquerque (ABQ) 8.8/10 Excellent! (1,005 reviews) Great stay! Good location near the Plaza, friendly staff, clean, comfortable rooms, and a great complimentary breakfast. Would definitely stay here again! Reviewed on Mar 21, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $1,346 per person Apr 30 - May 4 found 9 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9/10 Wonderful! (441 reviews) The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing Reviewed on Mar 27, 2026 ![The Hacienda & Spa at Hotel Santa Fe](https://images.trvl-media.com/lodging/1000000/810000/802700/802697/c5bd86f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Hacienda & Spa at Hotel Santa Fe Downtown Santa Fe CA $1,595 per person Apr 29 - May 3 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Albuquerque (ABQ) 9.4/10 Exceptional! (1,006 reviews) This was our best stay on a two month road trip. I can’t say enough how much we enjoyed this hotel and would give it six stars if I could. The facilities were excellent including a spacious room with a patio. What really made it special was the exceptionably friendly and helpful staff. Special thanks to Soriano for her help and friendly smile. We loved the evening happy hour, especially when it was on the upper patio. Reviewed on Mar 25, 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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) ## 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.