
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
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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.