Far North Side Ski Vacations
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Top Ski vacation packages in Far North Side
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥454,382
per person
Oct 1 - Oct 8
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
I’ve stayed at several hotels in this area and the Silversmith is by far the nicest. The hotel staff were very friendly and accommodating. The room was clean, comfortable and quiet. Highly recommend!
Reviewed on Aug 31, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
￥420,638
per person
Oct 1 - Oct 8
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,960 reviews)
Tiny tiny room . Barely big enough to move around bed. But great location !
Reviewed on Aug 31, 2026
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See all available trips from Osaka to Far North Side
View all trips5* Ski vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
￥490,370
per person
Nov 2 - Nov 6
found 8 hours ago
Roundtrip non-stop flight included
Osaka (OSA) 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
Four Seasons Hotel Chicago
Downtown Chicago
￥383,555
per person
Oct 3 - Oct 6
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The staff was so kind and helpful. Great location and dining options. The room was spotless and comfortable
Reviewed on Aug 30, 2026
Don't see what you're looking for?
See all available trips from Osaka to Far North Side
View all trips3 Night Ski vacations in Far North Side
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 Far North Side
View all trips4 Night Ski vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
￥490,370
per person
Nov 2 - Nov 6
found 8 hours ago
Roundtrip non-stop flight included
Osaka (OSA) 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 Far North Side
View all tripsThings 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.
