Southern Wisconsin Romantic Vacations

Book a Romantic Hotel + Flight or Car together to unlock savings

Photo by Evae
  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Romantic vacation packages in Southern Wisconsin

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥361,801
per person
Oct 18 - Oct 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
¥285,690
per person
Oct 18 - Oct 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
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 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥283,386
per person
Nov 2 - Nov 7
just found
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,311 reviews)
the bed was super comfy. hotel was clean and the staff were great! would definitely stay here again!

Reviewed on Aug 9, 2026

Don't see what you're looking for?
See all available trips from Osaka to Southern Wisconsin
View all trips

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 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥372,526
per person
Oct 18 - Oct 21
found 17 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
¥415,195
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips

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 17 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 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
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 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips

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 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 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
View all trips
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.