Historic Route 66 Ski Vacations
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Top Ski vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥298,767, price is now ￥224,794 per person
￥224,794
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.
Reviewed on Dec 31, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥253,246, price is now ￥194,618 per person
￥194,618
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room
Clean bathroom
Friendly staff
Reviewed on Jan 1, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥306,118, price is now ￥244,084 per person
￥244,084
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.
Reviewed on Dec 29, 2025
The Emily Hotel
Downtown Chicago
Price was ￥240,948, price is now ￥197,552 per person
￥197,552
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Had a great dinner at Fora before a very short walk to the new years eve event we were headed to and then came back for a great night's sleep in a very comfortable room! All the staff we interacted with were great!
Reviewed on Jan 1, 2026
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See all available trips from Osaka to Historic Route 66
View all trips5* Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥298,767, price is now ￥224,794 per person
￥224,794
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.
Reviewed on Dec 31, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥306,118, price is now ￥244,084 per person
￥244,084
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.
Reviewed on Dec 29, 2025
Don't see what you're looking for?
See all available trips from Osaka to Historic Route 66
View all trips3 Night Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥253,246, price is now ￥194,618 per person
￥194,618
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room
Clean bathroom
Friendly staff
Reviewed on Jan 1, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥298,767, price is now ￥224,794 per person
￥224,794
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.
Reviewed on Dec 31, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥306,118, price is now ￥244,084 per person
￥244,084
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.
Reviewed on Dec 29, 2025
Don't see what you're looking for?
See all available trips from Osaka to Historic Route 66
View all trips4 Night Ski vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Alsip
Price was ￥169,364, price is now ￥150,168 per person
￥150,168
per person
Feb 2 - Feb 6
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
Denise at the front desk was amazing!!! She went above and beyond with local recommendations. Booked our return stay with them simply because of her!!!
Reviewed on Dec 29, 2025
DoubleTree by Hilton Chicago - North Shore Conference Center
Price was ￥174,440, price is now ￥156,494 per person
￥156,494
per person
Feb 2 - Feb 6
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Decent and plenty. Good service.
Reviewed on Dec 31, 2025
Hilton Rosemont Chicago O'Hare
Price was ￥185,476, price is now ￥167,526 per person
￥167,526
per person
Feb 2 - Feb 6
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
The room and staff were extremely friendly, but I specifically requested a room with a bath so I could soak my leg after a surgery. There was absolutely no water pressure when it came to the bath and the drain wouldn't close all the way. For how much I paid I feel like I should have been able to take a bath
Reviewed on Dec 8, 2025
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See all available trips from Tokyo to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
