Historic Route 66 Beach Vacations

Book a Beach 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 Beach vacation packages in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥469,462, price is now ￥389,580 per person
￥389,580
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
The Riu in Chicago was in a great location downtown. The rooftop bar offered great views, drinks and food. The breakfast buffet was one of the best we've ever had. The room was clean and quiet. You can't ask for more!

Reviewed on Oct 28, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥428,908, price is now ￥391,593 per person
￥391,593
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥412,869, price is now ￥411,252 per person
￥411,252
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Breakfast

Reviewed on Oct 27, 2026

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.