Title: Kid friendly Vacations in Historic Route 66 2026/2026 | 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

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## Flight and Kid friendly 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

CA $500

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

great staff...loved our stay.

Reviewed on Nov 22, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=wfVl52Kb4qOSeVECiqdWnWuP4IUUN929xfZP45-7kFN9-FXh8i6OypWLaN2Nj_0r)

![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

CA $771

per person

Feb 12 - Feb 15

found 2 hours ago

Roundtrip flight included

Toronto (YTO) 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 Nov 26, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=povcxfI1kKc6tB2V7mz6EaNp3ENMM0zj2CZNpOMqxWZjEckb3RWBv68Udxv0dA2S)

![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 $677

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Its room was perfect the only bad part was their was a couple stains in the bathroom wall

Reviewed on Dec 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&HotelClass=40&dealMarker=wfVl52Kb4qOSeVECiqdWnVXPhmuheeTTVl3VBMUGmsp1qh7JmCiIV1n699b6lppd)

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $544

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (347 reviews)

Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.

Reviewed on Nov 25, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6P0CxjkGnW7N562c1ZrQZ5MQycwgm17GMUc2M7G22pDJ)

![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 $865

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

It is always an amazing place to stay

Reviewed on Nov 26, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6P0CxjkGnW7N562c1ZrQZ5PFx7vwHNBqqwFYiuD-2GdZ)

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/2026-01-02/2026-01-09/?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 $865

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

It is always an amazing place to stay

Reviewed on Nov 26, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=2MaV768TBcz8HM99OhHJ6P0CxjkGnW7N562c1ZrQZ5PFx7vwHNBqqwFYiuD-2GdZ)

![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 $1,369

per person

Feb 12 - Feb 16

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

The staff was amazing. Will be making a return stay.

Reviewed on Nov 30, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=2MaV768TBcz8HM99OhHJ6My9Aht2N4B94ODfy8EKvH6paFTZc0fdjD-2fA1SuY-B)

![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 $1,093

per person

Feb 27 - Mar 2

found 20 hours ago

Roundtrip flight included

Montreal (YUL) 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 Dec 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-27/2026-03-02/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=Iv3HNzwXsEvzE2M41LpVc9xAyOzgX3YTKIVp7payAHfgVoeHGzaCcto2id1QXV9W)

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/2026-01-02/2026-01-09/?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.

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $544

per person

Feb 12 - Feb 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Chicago (ORD)

9.2/10 Wonderful! (347 reviews)

Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.

Reviewed on Nov 25, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&HotelClass=40&dealMarker=2MaV768TBcz8HM99OhHJ6P0CxjkGnW7N562c1ZrQZ5MQycwgm17GMUc2M7G22pDJ)

![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

CA $771

per person

Feb 12 - Feb 15

found 2 hours ago

Roundtrip flight included

Toronto (YTO) 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 Nov 26, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&HotelClass=40&dealMarker=povcxfI1kKc6tB2V7mz6EaNp3ENMM0zj2CZNpOMqxWZjEckb3RWBv68Udxv0dA2S)

![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 $572

per person

Feb 12 - Feb 15

found 2 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Its room was perfect the only bad part was their was a couple stains in the bathroom wall

Reviewed on Dec 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&HotelClass=40&dealMarker=povcxfI1kKc6tB2V7mz6EaNp3ENMM0zj2CZNpOMqxWZzMzMahoSb2bWcj9TNFEST)

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/2026-01-02/2026-01-09/?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.

![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

CA $500

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

great staff...loved our stay.

Reviewed on Nov 22, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnWuP4IUUN929xfZP45-7kFN9-FXh8i6OypWLaN2Nj_0r)

![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 $677

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Its room was perfect the only bad part was their was a couple stains in the bathroom wall

Reviewed on Dec 1, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnVXPhmuheeTTVl3VBMUGmsp1qh7JmCiIV1n699b6lppd)

![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

CA $720

per person

Feb 12 - Feb 16

found 1 day ago

Roundtrip flight included

Toronto (YTO) 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 Nov 26, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnVXPhmuheeTTVl3VBMUGmsoFtupLpPPrSZTtmzyxUmmw)

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/2026-01-02/2026-01-09/?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.

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## 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.

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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

![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFPklEQVR4Xu3cTXLcNhCGYbi0mKWPMEfh0cCj8ShzBC+1UBlRf2j8EEPJ6VQ5C+l9Nxr1AHi4g5k4SeV/KK2DvxFIKJBQIKFAQoGEAgkFEgokFEgokFAgoUBCgYQCCQUSCiQUSCiQUCChQEKBhAIJBRIKJBRIKJBQIKFAQk3IW1q6t9GPUo50e1/8PlK/bLqV1/S+/WGfcx3N5XEySAJZl4HU8jgZJIGsy0BqeZz8VZE8ftOJw93q8FG3z4hv/GWP0jufBQICAmKBKBAF0vO16taRXL88bOoL9+TXvkYP++GIRueNFggIiP0AAUkgIN7niPLtt75wr2t8lQIBSSAgHshYpUBA0n9A9uQX+nxiKb/9rdt+f7EPIHeb7gnEj7VF4yMICMhRF4CAqBUZ+VpvqyOduKefE3Kvy4X0QDQC6YHU5SAgZT0LBGSc6AnJdbvf8Z+NlvI4GeRitJTHySAXo6U8Tga5GC3lcTLIxWgpj5NBLkZLeZwMcjFayuPkCblIri501Ufq/Pe7PgsE5CKQJRCQi0CWvi7iV/XT7b1p8XLHP+WrVB6HgoAokJqvUnkcCgKiQGq+SuVx6FdF9nqhb/W3R13to1f7/IT0jfrX0KVe+9qY/asCAqJAQAoICEhrQt7qmepWdKErP/HWF54fxTeOkf320r5TICAgICAagYB4K/Kzfvar+qWeWAxJ/UI3t+UDX6WNICAeCAiIBQLyRyS37X7Hz64tbte+/9dNepTeuPb1dFMgICCnkQKpi0HGR5DTSH0fxBvb96R/dn2YO23/7Y/SR3oR10Z/ulwXWiAgICAgICAfI36hH/bJejHE73ht18hPlGsnKv3hYLNPfVUPBASkfg0C0lb1QEDe6r08396jTYvriXvSte/uvT6dj7QKZNNikPERBARE2WcQWwxy+q1f1dqucr3Q5xP76JyeLvV386l1BFJAQJ5aRyAFBOSpdfR1kHntw67q8yt2R5I/iq1Kq+ujHgiIBwICAgKiJkTbhWi79dK/POxXd0s90Uc9Pd2tfP6KDdICAQEBsUBARoet9RP9jteJKd3rAt3xylZ5ze2reiAtEBAQkHaQB9L61oidqDvevqnl4te+ejyPlG9U/nRTICAFpICAgICMJmR5xe5zvU+XabTXw86rzvlZHggIyFUgIAUExL8YJ9qb8pv98Nvb37rT9CjvTe/TY5T+cMeDnEYgIAoEBKTt/7bIUU88J1f1Vel0xwsZT5fHNyAgIC2QOZACAuKIr7Vv6lq745Ujur3nR3nU+chHdpYHAgLSDm+BWCAFBOQyufNf5vKEKH+UXH9ztz+wBwJyEQgIiAUC8tYP8+423evnze54u71fbDT+oXdH5B5tq/4k0AMBAQGp3W26188gCgREa0eO9F6rq0fRW/dhiLmpb+zIGFkgBQRknHgMAySBgBQQ+8Lfp28V8dEP+/rV7nhvjLrrPbkWCAgICAgISAixC/23vWLb4tRfnvWKncztb92l3/H+dD0QEBAQkKMOQTYtTiC9jxC1afH7SGnVVl7rd0L0v9b6IBCNQEASCMhTIBqBjPxE2z6fONqmxXsbaZU2ToFoNNrbCGTePrdNi/c2Apm3z23T4r2NQObtc9u0eG8jkHn73DYt3tsIZN4+t02L9zb6F8i5u03t5Xm8YvdRsffpm/142FL7w8G44x927U+BFJDFAAEB8UDKt0f+XiChQEKBhAIJBRIKJBRIKJBQIKFAQoGEAgkFEgokFEgokFAgoUBCgYQCCQUSCiQUSCiQUCChQEKBhAIJ9XWQfwCYjF6z+3AaeAAAAABJRU5ErkJggg==)