Southern Wisconsin Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- 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
- Rest easyPlan, book, and manage your trip all in one place
Top Romantic vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
￥454,382
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
This was our second stay here this year. Had nice interactions with staff members and a clean room. Will return again!
Reviewed on Sep 1, 2026
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View all trips5* Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥359,054
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .
Reviewed on Sep 1, 2026
The Peninsula Chicago
Downtown Chicago
￥490,370
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,013 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 Tokyo to Southern Wisconsin
View all trips3 Night Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥359,054
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .
Reviewed on Sep 1, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥372,235
per person
Nov 2 - Nov 6
found 23 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .
Reviewed on Sep 1, 2026
Don't see what you're looking for?
See all available trips from Osaka 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.
