Far Southwest Side Ski Vacations
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Top Ski vacation packages in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥569,625, price is now ￥425,920 per person
￥425,920
per person
Oct 27 - Nov 1
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Amazing stay worth every penny
Reviewed on Sep 14, 2025
The Emily Hotel
Downtown Chicago
Price was ￥497,380, price is now ￥383,176 per person
￥383,176
per person
Oct 27 - Nov 1
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.
Reviewed on Sep 8, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥684,365, price is now ￥542,020 per person
￥542,020
per person
Oct 18 - Oct 23
found 2 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
Wonderful . Fresh towels, turn down service. Genuinely friendly employees. Pool and spa on site very very nice !
Reviewed on Sep 14, 2025
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View all trips5* Ski vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥569,625, price is now ￥425,920 per person
￥425,920
per person
Oct 27 - Nov 1
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Amazing stay worth every penny
Reviewed on Sep 14, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥684,365, price is now ￥542,020 per person
￥542,020
per person
Oct 18 - Oct 23
found 2 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
Wonderful . Fresh towels, turn down service. Genuinely friendly employees. Pool and spa on site very very nice !
Reviewed on Sep 14, 2025
The Langham, Chicago
Downtown Chicago
Price was ￥581,648, price is now ￥464,426 per person
￥464,426
per person
Oct 27 - Nov 1
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025
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View all trips3 Night Ski vacations in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Price was ￥356,486, price is now ￥297,642 per person
￥297,642
per person
Dec 1 - Dec 4
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.
Reviewed on Sep 8, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥408,054, price is now ￥327,779 per person
￥327,779
per person
Dec 1 - Dec 4
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Amazing stay worth every penny
Reviewed on Sep 14, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥508,173, price is now ￥411,262 per person
￥411,262
per person
Dec 1 - Dec 4
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,014 reviews)
Wonderful . Fresh towels, turn down service. Genuinely friendly employees. Pool and spa on site very very nice !
Reviewed on Sep 14, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Far Southwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
