Southern Wisconsin Romantic Vacations
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Top Romantic vacation packages in Southern Wisconsin
Price found within the past 48 hours. Click for updated prices.
Lodge Kohler
Price was ￥295,003, price is now ￥254,516 per person
￥254,516
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Green Bay (GRB)
9.6/10 Exceptional! (1,003 reviews)
Beautiful, clean and welcoming. We look forward to staying here again
Reviewed on Jan 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,704, price is now ￥319,797 per person
￥319,797
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥312,320, price is now ￥258,975 per person
￥258,975
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.
Reviewed on Jan 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥337,890, price is now ￥285,200 per person
￥285,200
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on Jan 18, 2026
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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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,704, price is now ￥319,797 per person
￥319,797
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥411,838, price is now ￥361,018 per person
￥361,018
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 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.
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was ￥242,208, price is now ￥217,552 per person
￥217,552
per person
Feb 20 - Feb 23
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Room was fantastic!! Staff was exceptional!!!
Fire alarms went off 3 times in the evening by because of an error with the system, but, they gave us a credit on our bill!! We plan on going back!
Reviewed on Jan 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥260,735, price is now ￥219,036 per person
￥219,036
per person
Mar 8 - Mar 11
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.
Reviewed on Jan 20, 2026
The Iron Horse Hotel
Fifth Ward
Price was ￥260,859, price is now ￥234,262 per person
￥234,262
per person
Feb 20 - Feb 23
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Breakfast came in a timely fashion and the food was great. Best bacon I’ve eaten in awhile.
Reviewed on Jan 20, 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥312,320, price is now ￥258,975 per person
￥258,975
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.
Reviewed on Jan 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,704, price is now ￥319,797 per person
￥319,797
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥337,890, price is now ￥285,200 per person
￥285,200
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on Jan 18, 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.
