Historic Route 66 Pet-friendly Holidays

Book a Pet-friendly Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Top flight + Pet-friendly hotel deals in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£896
per person
30 Dec - 5 Jan
found 17 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)
Great staff. Perfect downtown location!

Reviewed on 13 Oct 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,071
per person
21 Dec - 28 Dec
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Súper cerca a todas las atracciones de Chicago

Reviewed on 12 Oct 2026

Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,073
per person
21 Dec - 28 Dec
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (2,187 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
£1,013
per person
21 Dec - 28 Dec
found 15 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (2,414 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£1,237
per person
1 Dec - 7 Dec
found 1 day ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Don't see what you're looking for?
See all available trips from London to Historic Route 66
View all trips

5* Pet-friendly holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£1,331
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Service was superb. However, the mattress was too soft for me. The comforter has a bloody spot on it that should have been replaced.

Reviewed on 12 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,991
per person
23 Nov - 27 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great location

Reviewed on 12 Oct 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,383
per person
23 Nov - 27 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Don't see what you're looking for?
See all available trips from London to Historic Route 66
View all trips

3 Night Pet-friendly holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£925
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,727 reviews)
This is the only property right on Navy Pier! We were able to get many places with the help of public transportation! And it had a great view!

Reviewed on 12 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,167
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great location

Reviewed on 12 Oct 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
£949
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,163 reviews)
Don't see what you're looking for?
See all available trips from London to Historic Route 66
View all trips

4 Night Pet-friendly holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,038
per person
28 Dec - 1 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,068
per person
28 Dec - 1 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Súper cerca a todas las atracciones de Chicago

Reviewed on 12 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,991
per person
23 Nov - 27 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great location

Reviewed on 12 Oct 2026

Don't see what you're looking for?
See all available trips from London to Historic Route 66
View all trips

How to find a pet-friendly holiday in Historic Route 66

How can I book the best pet-friendly holidays in Historic Route 66?

As a pet parent, you want your best bud along for your Historic Route 66 holiday, right? So use our pet-friendly filter to find all the places that are purr-fect for cats, dogs or even well-trained rabbits. Think stacks of outside space, welcome treats and maybe something lovely that keeps the travel time to a minimum.

Can I book a cheap Historic Route 66 pet-friendly holiday?

pet-friendly package holidays start at £896, but prices and availability are subject to change, and additional terms may apply. To narrow down the best deals, sort by price and use the filters to find cheap places with tail-wag-worthy amenities.

How can I book holiday lets in Historic Route 66 that are pet friendly?

The space and seclusion of a holiday let is great for holidaying as a family or bigger group, and if your furry friends are with you, even better. Use both the private holiday home and pet-friendly filters to find all the options that tick both boxes.

How can I find pet-friendly holidays in Historic Route 66 with hot tubs?

Pet-friendly holidays aren’t just about the animals – you deserve to indulge yourself, too! Filter our Historic Route 66 properties using the hot-tub and pet-friendly holiday options and find somewhere you can relax while the pooches snooze.

Can I book a pet-friendly holiday in Historic Route 66 with a car?

For hassle-free pet-friendly travel, a car is a no-brainer. Book both your car hire and accommodation with Expedia and you’ll sniff out some great savings.

How can I book last-minute pet-friendly holidays in Historic Route 66?

A spontaneous last-minute getaway to Historic Route 66 with your pet is what holiday dreams are made of. You might even dig up discounted rates on some hotels by booking close to the date.

Can I book a pet-friendly holiday in Historic Route 66 with free cancellation and/or flexible dates?

We offer several places to stay with free cancellation in Historic Route 66, just use the fully refundable filter to find the ones available on your dates. Make sure you read the terms and conditions, too.

Why should I book Historic Route 66 pet-friendly travel with Expedia?

Thanks to our dedicated pet-friendly filter, it’s incredibly easy to find accommodation in Historic Route 66 that welcomes fur babies. Search, choose and book in just a few clicks. Purr-fect!

More holidays you might like

All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holiday packages
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Where to go when
Where to go when

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.