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.
Omni Chicago Hotel
Downtown Chicago
￥223,673
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,055 reviews)
Best stay experience this year . The concierge and the doormen were so helpful. The location is awesome and perfect for walking or hopping in an uber and getting anywhere down town in 5-10 min
Reviewed on Sep 19, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
￥295,616
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home
Reviewed on Sep 19, 2026
The Peninsula Chicago
Downtown Chicago
￥375,078
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
We had a spectacular stay! The service was truly first-class, and every member of the staff was incredibly friendly and welcoming. The restaurant servers were excellent, and the live music during lunch was one of the highlights of our stay.
Everything was spotless, and we were made to feel especially welcome while celebrating our anniversary. All of our special requests were handled perfectly, which made the experience even more memorable.
We would definitely stay here again the next time we’re in Chicago. Highly recommended!
Reviewed on Sep 20, 2026
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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
￥295,616
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home
Reviewed on Sep 19, 2026
The Peninsula Chicago
Downtown Chicago
￥375,078
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
We had a spectacular stay! The service was truly first-class, and every member of the staff was incredibly friendly and welcoming. The restaurant servers were excellent, and the live music during lunch was one of the highlights of our stay.
Everything was spotless, and we were made to feel especially welcome while celebrating our anniversary. All of our special requests were handled perfectly, which made the experience even more memorable.
We would definitely stay here again the next time we’re in Chicago. Highly recommended!
Reviewed on Sep 20, 2026
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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.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥295,616
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home
Reviewed on Sep 19, 2026
The Peninsula Chicago
Downtown Chicago
￥375,078
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
We had a spectacular stay! The service was truly first-class, and every member of the staff was incredibly friendly and welcoming. The restaurant servers were excellent, and the live music during lunch was one of the highlights of our stay.
Everything was spotless, and we were made to feel especially welcome while celebrating our anniversary. All of our special requests were handled perfectly, which made the experience even more memorable.
We would definitely stay here again the next time we’re in Chicago. Highly recommended!
Reviewed on Sep 20, 2026
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.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥328,884
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Place in the heart of the city. Accessable to all establishment. Staffs are great. Feels home
Reviewed on Sep 19, 2026
The Peninsula Chicago
Downtown Chicago
￥493,007
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
We had a spectacular stay! The service was truly first-class, and every member of the staff was incredibly friendly and welcoming. The restaurant servers were excellent, and the live music during lunch was one of the highlights of our stay.
Everything was spotless, and we were made to feel especially welcome while celebrating our anniversary. All of our special requests were handled perfectly, which made the experience even more memorable.
We would definitely stay here again the next time we’re in Chicago. Highly recommended!
Reviewed on Sep 20, 2026
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See all available trips from Osaka 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.
