Northwest Side Kid friendly Vacations
Book a Kid friendly Hotel + Flight or Car together to unlock savings
Top Kid friendly vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥632,616, price is now ￥511,244 per person
￥511,244
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Horrible, horrible housekeeping staff many times I had to have head of housekeeping come and monitor
Very disappointing
Reviewed on May 10, 2026
Swissotel - Chicago
Downtown Chicago
Price was ￥499,432, price is now ￥403,632 per person
￥403,632
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!
Reviewed on May 11, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥462,078, price is now ￥387,046 per person
￥387,046
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Clean rooms, friendly staff, great veiws especially from rooftop bar
Reviewed on May 11, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥501,385, price is now ￥421,470 per person
￥421,470
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
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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 ￥632,616, price is now ￥511,244 per person
￥511,244
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Horrible, horrible housekeeping staff many times I had to have head of housekeeping come and monitor
Very disappointing
Reviewed on May 10, 2026
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥639,790, price is now ￥584,960 per person
￥584,960
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Loved our suite- gorgeous views! Great service and excellent location
Reviewed on May 8, 2026
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View all trips4 Night Kid friendly vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was ￥437,988, price is now ￥354,950 per person
￥354,950
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!
Reviewed on May 11, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.