Southern Wisconsin Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
Photo by Evae
- 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.
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥509,188, price is now ￥479,348 per person
￥479,348
per person
Nov 29 - Dec 2
found 1 hour ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
It was a great stay and the staff was super friendly
Reviewed on Oct 30, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips5* Romantic vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
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.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was ￥448,726, price is now ￥412,772 per person
￥412,772
per person
Nov 29 - Dec 2
found 1 hour ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
The hotel is in a great location, about a block off Michigan Avenue. It is a charming old building, around a hundred years old. There was a bit of a problem, however, because of elevators. There are two, which is fine, but when one was out of commission for a spell, the waits were long.
Reviewed on Oct 30, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥546,545, price is now ￥474,103 per person
￥474,103
per person
Nov 29 - Dec 2
found 1 hour ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
Breakfast buffet was amazing. Would definitely stay here again.
Reviewed on Oct 30, 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.
