Northwest Side Kid friendly Vacations
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Top Kid friendly vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥338,022, price is now ￥229,282 per person
￥229,282
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Very clean room, friendly staff, wonderful breakfast!
Reviewed on Jan 22, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥450,632, price is now ￥332,884 per person
￥332,884
per person
Apr 1 - Apr 6
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
First time there. Staff was helpful and they provided excellent memorable service
Reviewed on Jan 20, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥407,761, price is now ￥319,483 per person
￥319,483
per person
Apr 1 - Apr 6
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room and the staff were wonderful!
Reviewed on Jan 22, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥474,268, price is now ￥392,745 per person
￥392,745
per person
Apr 1 - Apr 6
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026
Don't see what you're looking for?
See all available trips from Osaka to Northwest Side
View all trips5* Kid friendly vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥392,548, price is now ￥280,660 per person
￥280,660
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room and the staff were wonderful!
Reviewed on Jan 22, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥450,632, price is now ￥332,884 per person
￥332,884
per person
Apr 1 - Apr 6
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
First time there. Staff was helpful and they provided excellent memorable service
Reviewed on Jan 20, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥474,268, price is now ￥392,745 per person
￥392,745
per person
Apr 1 - Apr 6
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026
Don't see what you're looking for?
See all available trips from Osaka to Northwest Side
View all trips4 Night Kid friendly vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥280,580, price is now ￥218,642 per person
￥218,642
per person
Apr 15 - Apr 19
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Very clean room, friendly staff, wonderful breakfast!
Reviewed on Jan 22, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥355,298, price is now ￥283,356 per person
￥283,356
per person
Apr 15 - Apr 19
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room and the staff were wonderful!
Reviewed on Jan 22, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥301,372, price is now ￥247,984 per person
￥247,984
per person
Apr 15 - Apr 19
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
The staff was incredible and very prompt to all issues that arose during my stay.
Reviewed on Jan 22, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
