
Southern Wisconsin Ski Vacations
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Top Ski vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥272,410, price is now ¥188,740 per person
¥188,740
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Love the decor and style
Reviewed on Sep 12, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥460,254, price is now ¥301,832 per person
¥301,832
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago
Reviewed on Sep 12, 2025

The Emily Hotel
Downtown Chicago
Price was ¥415,042, price is now ¥291,500 per person
¥291,500
per person
Nov 12 - Nov 18
just found
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

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥314,632, price is now ¥221,254 per person
¥221,254
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
Very good location. Clean room. Staff very friendly and pleasant. Breakfast has a lot of options from fresh fruits to eggs to baked goods. Would stay again.
Reviewed on Sep 12, 2025

Pendry Chicago
Downtown Chicago
Price was ¥321,014, price is now ¥236,332 per person
¥236,332
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
This is an exceptional hotel. The rooms are clean. The service is impeccable, and the products!! The signature scent is to die for. It is now a part of my life. I had to buy a candle on the way out and have already visited the online store for body wash and lotion. Well done. There are a lot of choices in Chicago, but this is now my go to. Will definitely be back!
Reviewed on Sep 12, 2025
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View all trips5* Ski vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥460,254, price is now ¥301,832 per person
¥301,832
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago
Reviewed on Sep 12, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Ski vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.

Hilton Chicago O'Hare Airport
O'Hare
Price was ¥326,050, price is now ¥280,336 per person
¥280,336
per person
Oct 17 - Oct 21
found 12 hours ago
Roundtrip flight included
Nagoya (NGO) to Chicago (ORD)
8.2/10 Very Good! (2,121 reviews)
Great spot to stay near the airport, especially for a layover
Reviewed on Sep 12, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥518,452, price is now ¥428,637 per person
¥428,637
per person
Oct 19 - Oct 23
found 15 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago
Reviewed on Sep 12, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥400,543, price is now ¥351,583 per person
¥351,583
per person
Oct 19 - Oct 23
found 15 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
Very good location. Clean room. Staff very friendly and pleasant. Breakfast has a lot of options from fresh fruits to eggs to baked goods. Would stay again.
Reviewed on Sep 12, 2025
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See all available trips from Nagoya 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.