Southern Wisconsin Mountain Vacations
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Top Mountain vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥328,376
per person
Dec 26 - Dec 30
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 2026
Kinzie Hotel
Downtown Chicago
￥240,994
per person
Dec 26 - Dec 30
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,187 reviews)
Great location for walking the area. Close to River Walk and all surrounding attractions and restaurants.
Reviewed on Oct 11, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
￥302,188
per person
Nov 16 - Nov 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Lovely hotel with a great location. Kind staff. Only slight disappointment is that the fan in our bathroom did not work so it got a bit foggy. But outside of that very small thing this place was perfect.
Reviewed on Oct 11, 2026
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See all available trips from Tokyo to Southern Wisconsin
View all trips5* Mountain vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥328,376
per person
Dec 26 - Dec 30
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Mountain vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥328,376
per person
Dec 26 - Dec 30
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
This is one of the best Trump properties I've been to.
I know Trump Hotels' bar is high, but this is on another level.
Obviously, being a landmark in Chicago, location is the best in Chicago.
There is a Langham property right next to it, but this is it.
Rooms are well maintained, and the restaurants were excellent.
I hope to visit again soon.
Reviewed on Oct 12, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
