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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥318,861
per person
Oct 3 - Oct 8
found 11 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
8.2/10 Very Good! (2,879 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥378,106
per person
Oct 3 - Oct 8
found 11 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Hotel was so comfortable and the staff was so kind and professional. The best breakfast buffet i have seen at a hotel. The location couldn’t have been any better.

Reviewed on Aug 8, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
¥329,998
per person
Oct 3 - Oct 8
found 11 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
The best

Reviewed on Aug 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥361,801
per person
Oct 18 - Oct 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Great experience!

Reviewed on Aug 7, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥403,878
per person
Oct 3 - Oct 8
found 11 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)
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5* Romantic vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥361,801
per person
Oct 18 - Oct 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Great experience!

Reviewed on Aug 7, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥372,526
per person
Oct 18 - Oct 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
¥583,301
per person
Oct 3 - Oct 8
found 11 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
Don't see what you're looking for?
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3 Night Romantic vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
¥285,690
per person
Oct 18 - Oct 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥361,801
per person
Oct 18 - Oct 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Great experience!

Reviewed on Aug 7, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥300,438
per person
Oct 18 - Oct 21
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.

Reviewed on Aug 8, 2026

Don't see what you're looking for?
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4 Night Romantic vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥258,259
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Hotel was so comfortable and the staff was so kind and professional. The best breakfast buffet i have seen at a hotel. The location couldn’t have been any better.

Reviewed on Aug 8, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
¥271,031
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
The best

Reviewed on Aug 8, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥264,027
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Don't see what you're looking for?
See all available trips from Osaka to Southern Wisconsin
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.