Central Chicago Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 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 Ski vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
per person
Aug 31 - Sep 3
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
Great hotel with the exception of a terribly uncomfortable bed. The mattress was incredibly firm and difficult to sleep on.
Reviewed on Jul 21, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips5* Ski vacations in Central Chicago
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 Central Chicago
View all trips3 Night Ski vacations in Central Chicago
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 Central Chicago
View all trips4 Night Ski vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Downtown Chicago
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
Absolutely five stars! Everybody is so nice. They have best Service! The location is wonderful. And the room is clean.
Reviewed on Jul 21, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.