Great River Road Ski Vacations
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Top Ski vacation packages in Great River Road
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥309,912
per person
Oct 3 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Lobby smelt amazing right off the bat. All the staff everywhere were very helpful. Breakfast was very good with lots of options. Room was clean and very nice! I definitely recommend!
Reviewed on Aug 30, 2026
Swissotel - Chicago
Downtown Chicago
￥285,588
per person
Oct 3 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
This hotel is well-maintained with clean, quiet, well-appointed, spacious rooms. Some have very nice views of Chicago and/or the River and Lake Michigan. The staff members were friendly and helpful, although I think I'm going to have to call them to get an itemized bill for my incidental room charges (usually such bills are emailed). This might be because I booked through Expedia. The location is great for exploring the loop as well as River North. I will definitely consider staying there again.
Reviewed on Aug 31, 2026
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View all trips5* Ski vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
￥1,131,944
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 2026
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See all available trips from Osaka to Great River Road
View all trips3 Night Ski vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥309,912
per person
Oct 3 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Lobby smelt amazing right off the bat. All the staff everywhere were very helpful. Breakfast was very good with lots of options. Room was clean and very nice! I definitely recommend!
Reviewed on Aug 30, 2026
Swissotel - Chicago
Downtown Chicago
￥285,588
per person
Oct 3 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
This hotel is well-maintained with clean, quiet, well-appointed, spacious rooms. Some have very nice views of Chicago and/or the River and Lake Michigan. The staff members were friendly and helpful, although I think I'm going to have to call them to get an itemized bill for my incidental room charges (usually such bills are emailed). This might be because I booked through Expedia. The location is great for exploring the loop as well as River North. I will definitely consider staying there again.
Reviewed on Aug 31, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Great River Road
View all trips4 Night Ski vacations in Great River Road
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥292,602
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Lobby smelt amazing right off the bat. All the staff everywhere were very helpful. Breakfast was very good with lots of options. Room was clean and very nice! I definitely recommend!
Reviewed on Aug 30, 2026
Don't see what you're looking for?
See all available trips from Osaka to Great River Road
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
