South Side 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 South Side
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Accommodations were great. Clean rooms and very convenient location. Service at the bar upstairs was pretty terrible the night we were there. Very unengaged and getting a drink took over 30 minutes
Reviewed on Jul 20, 2025
5* Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
3 Night Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Accommodations were great. Clean rooms and very convenient location. Service at the bar upstairs was pretty terrible the night we were there. Very unengaged and getting a drink took over 30 minutes
Reviewed on Jul 20, 2025
4 Night Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.