Historic Route 66 Pet-friendly Holidays

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    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
£427
per person
30 Sept - 3 Oct
found 10 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£558
per person
30 Sept - 3 Oct
found 10 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
N/a

Reviewed on 18 Aug 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£435
per person
30 Sept - 3 Oct
found 10 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
The hotel is in a good location, making walking to many sites possible. Room was fine, but snug. Hallways are ridiculously tight. No breakfast included. Parking is crazy expensive, but trying to drive the city is worse!!

Reviewed on 18 Aug 2026

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

Downtown Chicago
£446
per person
30 Sept - 3 Oct
found 10 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
9.2/10 Wonderful! (2,768 reviews)
Very nice hotel in the heart of River North in Chicago. Close to the bars and restaurants of River North and also easy walk over to Michigan Avenue. Hotel was very well maintained and the room amenities were very nice. The staff was great, especially the person who checked me in, but every interaction I had was positive. Thanks!

Reviewed on 18 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
£610
per person
30 Sept - 3 Oct
found 10 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Loved the location. Was able to park in the parking ramp, leave the car, and walk to many, many places! Room was clean, view was excellent, and choices of food/snacks was endless!

Reviewed on 18 Aug 2026

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5* Pet-friendly holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£819
per person
30 Sept - 3 Oct
found 3 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
£2,324
per person
26 Sept - 2 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£1,889
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
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3 Night Pet-friendly holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
£435
per person
30 Sept - 3 Oct
found 10 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
8.4/10 Very good! (2,089 reviews)
The hotel is in a good location, making walking to many sites possible. Room was fine, but snug. Hallways are ridiculously tight. No breakfast included. Parking is crazy expensive, but trying to drive the city is worse!!

Reviewed on 18 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£558
per person
30 Sept - 3 Oct
found 10 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
N/a

Reviewed on 18 Aug 2026

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

Downtown Chicago
£446
per person
30 Sept - 3 Oct
found 10 hours ago
Return flight included
Austin (AUS) to Chicago (ORD)
9.2/10 Wonderful! (2,768 reviews)
Very nice hotel in the heart of River North in Chicago. Close to the bars and restaurants of River North and also easy walk over to Michigan Avenue. Hotel was very well maintained and the room amenities were very nice. The staff was great, especially the person who checked me in, but every interaction I had was positive. Thanks!

Reviewed on 18 Aug 2026

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4 Night Pet-friendly holidays in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,153
per person
1 Oct - 5 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on 17 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,297
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
N/a

Reviewed on 18 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,250
per person
22 Oct - 26 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Overall, this is a great hotel. My family loved the rooms and the fitness center. The staff were mostly great too. We will definitely stay here again if we come back to Chicago. We were given rooms that were 28 floors apart despite making our reservation months in advance. Yes, it was one reservation which included 2 rooms. Both the shower and toilet space was fairly tight. Other than that, we are very happy.

Reviewed on 18 Aug 2026

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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 £427, 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

* 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.