Historic Route 66 Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Ski vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
￥1,034,982
per person
Nov 9 - Nov 13
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
This property was the perfect choice four our trip because we had a view of the river walk and Navy Pier on the lake. We didn’t hear any loud or obnoxious sounds while we were sleeping or relaxing! The staff were super helpful had great customer service!
Reviewed on Sep 30, 2026
Don't see what you're looking for?
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.
Don't see what you're looking for?
See all available trips from Tokyo 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.
Don't see what you're looking for?
See all available trips from Fukuoka 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.
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.
