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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥445,300, price is now ￥365,962 per person
￥365,962
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥619,042, price is now ￥484,597 per person
￥484,597
per person
Jul 26 - Jul 31
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Incredible everything
Reviewed on May 8, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥717,300, price is now ￥562,296 per person
￥562,296
per person
Jul 26 - Jul 31
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Smelly hotel, unfriendly night time front desk staff. The AV did not work.
Reviewed on May 8, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥689,825, price is now ￥554,748 per person
￥554,748
per person
Jul 26 - Jul 31
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 2026
The Langham, Chicago
Downtown Chicago
Price was ￥705,634, price is now ￥574,592 per person
￥574,592
per person
Jul 26 - Jul 31
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Great accommodation and staff attention
Reviewed on May 8, 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥619,042, price is now ￥484,597 per person
￥484,597
per person
Jul 26 - Jul 31
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Incredible everything
Reviewed on May 8, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥717,300, price is now ￥562,296 per person
￥562,296
per person
Jul 26 - Jul 31
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Smelly hotel, unfriendly night time front desk staff. The AV did not work.
Reviewed on May 8, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥689,825, price is now ￥554,748 per person
￥554,748
per person
Jul 26 - Jul 31
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Wonderful Hotel will definitely be looking forward to going back.
Reviewed on Apr 25, 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.
Chicago Marriott Downtown Magnificent Mile
Downtown Chicago
Price was ￥399,876, price is now ￥332,300 per person
￥332,300
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
Patrick was excellent at check in despite how busy it was. I felt the staff handled the crush of people efficiently and pleasantly. I was pleasantly surprised I received $15 per day towards the bar or snack room. The snack room selections included hot and cold items.
My room was a bit hot for my taste and they took care of it immediately.
Reviewed on May 3, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥445,300, price is now ￥365,962 per person
￥365,962
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Swissotel - Chicago
Downtown Chicago
Price was ￥406,322, price is now ￥337,637 per person
￥337,637
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
Picked the hotel because it was supposed to be near Riviera theater. It really wasn't. Otherwise, it's a beautiful property. Staff are friendly and helpful. There's casual and fine dining at the location. Easy to get a cab if you don't have an app. Across from riverfront.
Reviewed on May 9, 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.
