Title: Kid friendly Vacations in Historic Route 66 2025/2026 | 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 Kid friendly Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 Kid friendly hotel deals in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 $1,034 per person Dec 23 - Dec 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=nydeEVrW5r1JKFwu4YZKCvtMlth0dv8UMcriRzUaZrh5-eYmRTAfD07qOq-4C3OO) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $1,071 per person Dec 21 - Dec 26 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 8.8/10 Excellent! (1,046 reviews) One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done. Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-21/2025-12-26/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&HotelClass=40&dealMarker=eQ41785sc6bOv5L8pbLHTsdFAkwIXJpCNUg_stgAkU5meMMDdRnkUapXCl-4Yamp) ![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 $1,706 per person Dec 23 - Dec 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=nydeEVrW5r1JKFwu4YZKClROWRUzfON2iL6IfXopJJ5sEVfrpwV5oHcsZS1GnBjx) ![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 $1,472 per person Jan 4 - Jan 11 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Albuquerque (ABQ) 8.8/10 Excellent! (1,022 reviews) The most amazing thing at the Inn at Vanessie was the food. The chicken enchiladas were fabulous. Breakfast was a delightful surprise. We were expecting coffee and a pastry, but it was a full buffet breakfast, and was very good. The room was ok, but the lighting in the bathroom was almost non-existent. The bed was firm, but comfortable. The staff were friendly and helpful. Reviewed on Oct 12, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-04/2026-01-11/?FromAirport=YVR&Destination=ABQ&NumRoom=1&NumAdult=2&NumChild=0&hotelId=85222&paandie=true&HotelClass=40&dealMarker=4BL55MylbzQdiPeKmhSoTHkpxwcdTm0LbTQqVIwRAIfGxiZglbASYsJTXMlgaTW3) ![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 $1,176 per person Nov 26 - Nov 29 found 12 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Excellent staff, check in process and dining experiences all superb! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-26/2025-11-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=40&dealMarker=PA3FMZb837eT9WkrMtHjEt53tpurMd8dkHjW8GbFjD_XRZH1CebTcqIq1PJJ9yvY) 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/2025-11-17/2025-11-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Kid friendly 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 CA $1,073 per person Dec 17 - Dec 20 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-17/2025-12-20/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=j-wMUwZ57PH9L72rnYZbVvKT7gOfG-8fU3MNEEFTc27P2Z3iNeGc7etW7b8JHBB7) ![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 $1,706 per person Dec 23 - Dec 28 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=nydeEVrW5r1JKFwu4YZKClROWRUzfON2iL6IfXopJJ5sEVfrpwV5oHcsZS1GnBjx) ![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 $1,176 per person Nov 26 - Nov 29 found 12 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Excellent staff, check in process and dining experiences all superb! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-26/2025-11-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=50&dealMarker=PA3FMZb837eT9WkrMtHjEt53tpurMd8dkHjW8GbFjD_XRZH1CebTcqIq1PJJ9yvY) 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/2025-11-17/2025-11-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Kid friendly holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![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 $657 per person Dec 12 - Dec 15 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=fGBlmbDjOackFL1GOo3Vlv4ATXbGvrI_G_i3eWAxcXET2b1vbMLg_FFbKdr_LeQX) ![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 $1,176 per person Nov 26 - Nov 29 found 12 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Excellent staff, check in process and dining experiences all superb! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-26/2025-11-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=40&dealMarker=PA3FMZb837eT9WkrMtHjEt53tpurMd8dkHjW8GbFjD_XRZH1CebTcqIq1PJJ9yvY) ![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 CA $1,073 per person Dec 17 - Dec 20 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-17/2025-12-20/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=j-wMUwZ57PH9L72rnYZbVvKT7gOfG-8fU3MNEEFTc27P2Z3iNeGc7etW7b8JHBB7) 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/2025-11-17/2025-11-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Kid friendly 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 $823 per person Dec 29 - Jan 2 found 12 hours ago Roundtrip flight included Calgary (YYC) to Chicago (ORD) 9/10 Wonderful! (698 reviews) Great apartment in a very nice area of the city. Nice workout space and pool too. Clean and very comfy rooms! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&dealMarker=jLTYrGR6efIIdRzNb1L-RmEh3yVRHQEnOkmL_lEi_3d2CFRV4VWv50ZyZBzqPUoA) ![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 $1,518 per person Nov 24 - Nov 28 found 1 hour ago Roundtrip non-stop flight included Toronto (YTZ) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=xZoNbKkeuKvO5NyJjEe0_1ogJGIJ1pzxLeoXUKLbtaeQOBJsLwec-JcHP6I4IEjX) ![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 CA $1,425 per person Dec 17 - Dec 21 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-17/2025-12-21/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=wd6j9t04FAC_ewFhHlfItuy5s3D-SBTH8Kq5NE7QiCCP5keqFSbmm-OpgySrvlKU) 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/2025-11-17/2025-11-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect family-friendly vacation in Historic Route 66 with Expedia #### What are some benefits of booking a family-friendly vacation? Whether it's luxurious or cheap, family vacations in Historic Route 66 are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships. #### How can I find the best family-friendly vacations? Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Historic Route 66. #### Are there cheap family vacations to Historic Route 66? Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard. #### When should I book family-friendly vacation packages? The right time to book family-friendly vacation packages in Historic Route 66 depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example. #### Can I book an all-inclusive family vacation in Historic Route 66? Yes, you'll find plenty of all-inclusive family vacation packages for Historic Route 66. To see what's available, just select the all-inclusive filter on your search. #### How can I book the best family activity vacation? If you're looking to make the most out of the available activities in Historic Route 66, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Historic Route 66 or something a bit more relaxed. #### Can I find luxury family vacations in Historic Route 66? If you're looking for a luxury family vacation to Historic Route 66, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line. #### How can I search for family vacation deals? Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Historic Route 66. #### Can I book a family vacation package that is fully refundable? If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Historic Route 66 are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking. #### Why should I book my family trip with Expedia? When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings. ## 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 Kid friendly Vacation Destinations > - 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[Family vacations in Tuscany](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/601686/Tuscany) > - [Family vacations in Panama](https://www.expedia.ca/lp/theme-vacations/kid-friendly-vacations/142/Panama) ## 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. 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