Southern Wisconsin Kid friendly Vacations

Book a Kid friendly 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 Kid friendly vacation packages in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥207,940
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥317,118
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
¥369,470
per person
Oct 20 - Oct 23
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Comfortable room with a great view and luxuriously soft bed!

Reviewed on Sep 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥208,690
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Na

Reviewed on Sep 13, 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
¥227,166
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips

5* Kid friendly 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
¥317,118
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥425,000
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥388,372
per person
Nov 18 - Nov 22
just found
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Southern Wisconsin
View all trips

3 Night Kid friendly 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
¥275,053
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥337,168
per person
Oct 20 - Oct 23
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Na

Reviewed on Sep 13, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
¥369,470
per person
Oct 20 - Oct 23
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Comfortable room with a great view and luxuriously soft bed!

Reviewed on Sep 13, 2026

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

4 Night Kid friendly 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
¥250,301
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Na

Reviewed on Sep 13, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥317,118
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥255,856
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
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.