West Side Ski Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Ski vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥358,086, price is now ￥306,858 per person
￥306,858
per person
Aug 16 - Aug 20
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Excellent customer service, amazing staff!
Reviewed on Jul 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥632,118, price is now ￥535,330 per person
￥535,330
per person
Aug 11 - Aug 17
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
We generally stay here when we travel to Chicago by the quality of service has diminished lately. Additionally if your booking is through Expedia, everything gets complicated and not well treated.
Reviewed on Jul 5, 2026
5* Ski vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥520,760, price is now ￥477,816 per person
￥477,816
per person
Aug 8 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
3 Night Ski vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥580,704, price is now ￥522,144 per person
￥522,144
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
4 Night Ski vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥513,962, price is now ￥426,949 per person
￥426,949
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Clean rooms staff were friendly and location was central. Beautiful bar and cities scenic view was perfect
Reviewed on Jul 4, 2026
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,853
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
