Southern Wisconsin Luxury Vacations
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Top Luxury vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥286,676, price is now ￥244,713 per person
￥244,713
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Amenities, very clean, wonderful buffet service.
Reviewed on Dec 20, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥405,962, price is now ￥330,854 per person
￥330,854
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!
Reviewed on Dec 19, 2025
Pendry Chicago
Downtown Chicago
Price was ￥325,747, price is now ￥269,370 per person
￥269,370
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Excellent location to stay in the heart of the city.
Reviewed on Dec 17, 2025
Hilton Chicago
Downtown Chicago
Price was ￥314,266, price is now ￥267,266 per person
￥267,266
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Great stay, lovely hotel. Great staff all around, Hannah upgraded our room to a 2 bathroom 2 bed with no charge after seeing we had a 4 party guest reservation. Definitely will be staying here again
Reviewed on Dec 20, 2025
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View all trips5* Luxury vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥405,962, price is now ￥330,854 per person
￥330,854
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!
Reviewed on Dec 19, 2025
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥366,234, price is now ￥333,728 per person
￥333,728
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Very nice amenities and wellness facility. High end shopping within a very short walk.
Reviewed on Dec 16, 2025
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See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Luxury vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥293,078, price is now ￥246,075 per person
￥246,075
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (326 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥405,962, price is now ￥330,854 per person
￥330,854
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!
Reviewed on Dec 19, 2025
Hilton Chicago
Downtown Chicago
Price was ￥314,266, price is now ￥267,266 per person
￥267,266
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Great stay, lovely hotel. Great staff all around, Hannah upgraded our room to a 2 bathroom 2 bed with no charge after seeing we had a 4 party guest reservation. Definitely will be staying here again
Reviewed on Dec 20, 2025
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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.
