West Side Kid friendly Vacations
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Top Kid friendly vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥255,656, price is now ￥217,333 per person
￥217,333
per person
Apr 2 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast options had a variety of foods available and the orange juice seemed very fresh.
Reviewed on Jan 19, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,778, price is now ￥333,140 per person
￥333,140
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥358,425, price is now ￥312,872 per person
￥312,872
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on Jan 18, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥411,838, price is now ￥361,018 per person
￥361,018
per person
Mar 15 - Mar 19
just found
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
5* Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,778, price is now ￥333,140 per person
￥333,140
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥411,838, price is now ￥361,018 per person
￥361,018
per person
Mar 15 - Mar 19
just found
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
3 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥356,674, price is now ￥296,962 per person
￥296,962
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast options had a variety of foods available and the orange juice seemed very fresh.
Reviewed on Jan 19, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,778, price is now ￥333,140 per person
￥333,140
per person
Mar 14 - Mar 17
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
4 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥312,320, price is now ￥258,975 per person
￥258,975
per person
Mar 15 - Mar 19
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Breakfast options had a variety of foods available and the orange juice seemed very fresh.
Reviewed on Jan 19, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,704, price is now ￥319,797 per person
￥319,797
per person
Mar 15 - Mar 19
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
