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.
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥250,934, price is now ￥216,740 per person
￥216,740
per person
May 22 - May 25
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,231 reviews)
Everything went pretty well. Glad we choose to stay there.
Reviewed on Mar 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥329,977, price is now ￥250,792 per person
￥250,792
per person
May 21 - May 24
found 2 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.
Reviewed on Mar 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥592,846, price is now ￥476,278 per person
￥476,278
per person
May 27 - Jun 1
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥292,366, price is now ￥248,644 per person
￥248,644
per person
May 21 - May 24
found 2 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
Clean room , lovely staff and great location
Reviewed on Mar 19, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips5* Cheap vacations in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥592,846, price is now ￥476,278 per person
￥476,278
per person
May 27 - Jun 1
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
Don't see what you're looking for?
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.
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥250,934, price is now ￥216,740 per person
￥216,740
per person
May 22 - May 25
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,231 reviews)
Everything went pretty well. Glad we choose to stay there.
Reviewed on Mar 15, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥363,834, price is now ￥287,560 per person
￥287,560
per person
May 22 - May 25
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 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.
