Great River Road 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 Great River Road
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥372,235
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Everything was excellent. Very clean. Staff members all very nice! Our view was the best!
Reviewed on Aug 30, 2026
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See all available trips from Tokyo to Great River Road
View all trips5* Ski vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥372,235
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Everything was excellent. Very clean. Staff members all very nice! Our view was the best!
Reviewed on Aug 30, 2026
The Peninsula Chicago
Downtown Chicago
￥1,131,944
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 2026
Don't see what you're looking for?
See all available trips from Osaka to Great River Road
View all trips3 Night Ski vacations in Great River Road
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 Great River Road
View all trips4 Night Ski vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥372,235
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Everything was excellent. Very clean. Staff members all very nice! Our view was the best!
Reviewed on Aug 30, 2026
Don't see what you're looking for?
See all available trips from Osaka to Great River Road
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
