Southern Wisconsin Cheap Vacations
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Top Cheap vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥553,760, price is now ￥380,458 per person
￥380,458
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.2/10 Very Good! (2,858 reviews)
Rooms were very bare. Ours didn’t even have a fridge, we had to ask for one. Then they gave us a beverage fridge. No dresser or storage anywhere. Bathroom had no counter space. Shower would get water everywhere because the curtain wasn’t long enough. Super tight space not worth the price.
Reviewed on Jul 30, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥638,004, price is now ￥410,090 per person
￥410,090
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Fue solo una noche, pero todo fue 100/10.
Reviewed on Jul 30, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥549,570, price is now ￥411,724 per person
￥411,724
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Excellent location
Reviewed on Jul 30, 2026
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View all trips5* Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
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See all available trips from Tokyo to Southern Wisconsin
View all trips3 Night Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was ￥442,264, price is now ￥363,128 per person
￥363,128
per person
Oct 6 - Oct 9
found 14 hours ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,144 reviews)
The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.
Reviewed on Jul 28, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips4 Night Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥378,943, price is now ￥301,171 per person
￥301,171
per person
Sep 8 - Sep 12
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
Fue solo una noche, pero todo fue 100/10.
Reviewed on Jul 30, 2026
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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.
