Central Chicago Ski Vacations
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Top Ski vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥266,548, price is now ￥215,022 per person
￥215,022
per person
Mar 24 - Mar 28
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast was great, room was super nice and upgraded
Reviewed on Jan 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥363,190, price is now ￥274,446 per person
￥274,446
per person
Mar 24 - Mar 28
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥271,462, price is now ￥219,834 per person
￥219,834
per person
Mar 24 - Mar 28
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Chicago Marriott Suites O'Hare
Price was ￥384,612, price is now ￥321,928 per person
￥321,928
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The staff were friendly and professional. The room was clean and as expected. Only drawback was the lack of amenities. Coffee was out of a machine in lobby and cost $4 - WiFi was not free and $15 a day.
Reviewed on Dec 28, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips5* Ski vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥363,190, price is now ￥274,446 per person
￥274,446
per person
Mar 24 - Mar 28
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips3 Night Ski vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Suites O'Hare
Price was ￥384,612, price is now ￥321,928 per person
￥321,928
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The staff were friendly and professional. The room was clean and as expected. Only drawback was the lack of amenities. Coffee was out of a machine in lobby and cost $4 - WiFi was not free and $15 a day.
Reviewed on Dec 28, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥471,930, price is now ￥365,182 per person
￥365,182
per person
Feb 20 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips4 Night Ski vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥266,548, price is now ￥215,022 per person
￥215,022
per person
Mar 24 - Mar 28
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast was great, room was super nice and upgraded
Reviewed on Jan 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥363,190, price is now ￥274,446 per person
￥274,446
per person
Mar 24 - Mar 28
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥271,462, price is now ￥219,834 per person
￥219,834
per person
Mar 24 - Mar 28
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
