Historic Route 66 Pet-friendly Vacations

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

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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

Top Pet-friendly vacation packages in Historic Route 66

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

Swissotel - Chicago

Downtown Chicago
¥264,532
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥269,632
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
The Cheshire

The Cheshire

¥324,782
per person
Nov 18 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to St. Louis (STL)
8.8/10 Excellent! (1,011 reviews)
Kinzie Hotel

Kinzie Hotel

Downtown Chicago
¥270,010
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,187 reviews)
Amazing hotel!

Reviewed on Oct 13, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥274,482
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
My biggest issue here is the room I was given, 801. Just not a nice room at all. It's tiny, it had a stale odour, no table/chair, its gloomy, its location, it's a bathtub, not a standalone shower, the mechanics of the door.... If I can say one thing, it is that the bed was comfortable and the fixtures in the bathroom look new. It's just not a place you want to spend any time. The second issue was the length of time to get room service. After many hours of travel, I was too tired to eat out anywhere. I ordered room service and the food was stone cold. The only edible part was the skinny fires that came with the burger. BTW, would be helpful to list the side on the order form as it just said burger... so I ordered separate fries which couldn't be eaten because they were not warm.

Reviewed on Oct 13, 2026

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

5* Pet-friendly vacations in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥379,986
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
This hotel is simply the best hotel I’ve ever stayed at, the building is beautiful, but the staff made it amazing. Absolutely superb

Reviewed on Oct 13, 2026

Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
¥533,310
per person
Nov 28 - Dec 3
found 23 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
Excellent experience. I’d recommend this property for their outstanding service and updated rooms.

Reviewed on Oct 9, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥491,986
per person
Nov 28 - Dec 3
found 23 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great location

Reviewed on Oct 12, 2026

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

3 Night Pet-friendly vacations 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
¥235,566
per person
Nov 21 - Nov 24
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (3,105 reviews)
The staff was extremely accommodating, it was marathon week so I understand things can be tough, my issues were with the room as a whole. The shower would leak into the bathroom and completely cover the floor and when I informed staff I was having flooding problems they said oh it’s the shower curtain as if it’s a common issue. The wall paper in the bathroom was peeling off the wall. Tv guide didn’t work so you get to play channel roulette. On the plus side staff was great and they provided cold drinks in the morning, ac works really well

Reviewed on Oct 14, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
¥236,139
per person
Nov 21 - Nov 24
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
Great stay

Reviewed on Oct 13, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥256,322
per person
Nov 21 - Nov 24
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
My biggest issue here is the room I was given, 801. Just not a nice room at all. It's tiny, it had a stale odour, no table/chair, its gloomy, its location, it's a bathtub, not a standalone shower, the mechanics of the door.... If I can say one thing, it is that the bed was comfortable and the fixtures in the bathroom look new. It's just not a place you want to spend any time. The second issue was the length of time to get room service. After many hours of travel, I was too tired to eat out anywhere. I ordered room service and the food was stone cold. The only edible part was the skinny fires that came with the burger. BTW, would be helpful to list the side on the order form as it just said burger... so I ordered separate fries which couldn't be eaten because they were not warm.

Reviewed on Oct 13, 2026

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

4 Night Pet-friendly vacations 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
¥236,203
per person
Nov 20 - Nov 24
found 17 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
Great stay

Reviewed on Oct 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥252,838
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
¥247,444
per person
Dec 25 - Dec 29
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.