Historic Route 66 Ski Vacations
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Top Ski vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥355,048
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
A very pretty hotel that is clean and has nice restaurants. The free breakfast buffet is unreal!
Reviewed on Aug 12, 2026
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See all available trips from Tokyo to Historic Route 66
View all trips5* Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago
Downtown Chicago
￥390,758
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
We had a terrific weekend stay! The staff was so friendly and the room was wonderful with a very comfortable bed. Location is very convenient, as well.
Reviewed on Aug 10, 2026
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See all available trips from Osaka to Historic Route 66
View all trips3 Night Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥355,048
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
A very pretty hotel that is clean and has nice restaurants. The free breakfast buffet is unreal!
Reviewed on Aug 12, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips4 Night Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥368,704
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
A very pretty hotel that is clean and has nice restaurants. The free breakfast buffet is unreal!
Reviewed on Aug 12, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
￥342,321
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)
This hotel has the worst elevator system I’ve ever experienced. I wouldn’t stay again based on the elevators. Yes they have a great rooftop but it took nearly 40 minutes to get down from the 21st floor due to only two elevators.
Reviewed on Aug 12, 2026
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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.
