South Side 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 South Side
Price found within the past 48 hours. Click for updated prices.
5* Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
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
3 Night Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
4 Night Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
