Southern Wisconsin Kid friendly Vacations

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Top Kid friendly vacation packages in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Ivy Boutique Hotel

Ivy Boutique Hotel

Downtown Chicago
¥438,505
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,431 reviews)
Nice location. Only concern was my bed seemed very old and really should be replaced.

Reviewed on Sep 11, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥626,188
per person
Nov 18 - Nov 22
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago
¥551,993
per person
Nov 18 - Nov 22
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,008 reviews)
AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown

Downtown Chicago
¥554,988
per person
Nov 18 - Nov 22
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
Accommodations were nice, but there was a little wear on the blackout curtains. Staff was extremely helpful and courteous. I will stay here again

Reviewed on Sep 10, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

Downtown Chicago
¥453,880
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
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5* Kid friendly vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago

The Peninsula Chicago

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥626,188
per person
Nov 18 - Nov 22
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
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3 Night Kid friendly vacations in Southern Wisconsin

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

The Talbott, Autograph Collection

Downtown Chicago
¥208,225
per person
Nov 19 - Nov 22
found 19 hours 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
¥275,053
per person
Nov 19 - Nov 22
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
¥227,166
per person
Nov 19 - Nov 22
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
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4 Night Kid friendly vacations in Southern Wisconsin

Price found within the past 48 hours. Click for updated prices.
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago
¥551,993
per person
Nov 18 - Nov 22
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,008 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥626,188
per person
Nov 18 - Nov 22
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown

Downtown Chicago
¥554,988
per person
Nov 18 - Nov 22
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
Accommodations were nice, but there was a little wear on the blackout curtains. Staff was extremely helpful and courteous. I will stay here again

Reviewed on Sep 10, 2026

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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.