Chicago Kid friendly Vacations
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Top Kid friendly vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was ￥213,320, price is now ￥178,333 per person
￥178,333
per person
Nov 1 - Nov 4
found 5 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,922 reviews)
It was a pleasurable stay
Reviewed on Sep 25, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Price was ￥272,392, price is now ￥228,168 per person
￥228,168
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,962 reviews)
A wonderful place with a fascinating history.
Reviewed on Sep 24, 2025
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Price was ￥291,798, price is now ￥248,366 per person
￥248,366
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (4,926 reviews)
Could have used more towels without having to ask for them . They gave us an issue for breakfast trying to order more than one omelette due to having a sick child in the room .
Also, we were expecting a hot tub . It would make the pool so much better .
Reviewed on Sep 24, 2025
Hyatt Regency Chicago
Downtown Chicago
Price was ￥219,386, price is now ￥190,997 per person
￥190,997
per person
Nov 1 - Nov 4
found 5 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.2/10 Wonderful! (3,346 reviews)
Our stay at the Hyatt Regency Chicago was absolutely amazing! The hotel was spotless, and the cleanliness throughout really stood out. Every staff member we encountered was professional, friendly, and went out of their way to make us feel welcome.
We loved the convenience of having plenty of on-site food options, which made it easy to grab a quick bite or sit down for a nice meal without leaving the property. The location couldn’t be better—just steps away from the Magnificent Mile and close to so many of Chicago’s top tourist attractions.
Overall, the Hyatt Regency Chicago exceeded our expectations, and we’ll definitely stay here again on our next trip!
Reviewed on Sep 23, 2025
3 Night Kid friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
Downtown Chicago
Price was ￥213,320, price is now ￥178,333 per person
￥178,333
per person
Nov 1 - Nov 4
found 5 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,922 reviews)
It was a pleasurable stay
Reviewed on Sep 25, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Price was ￥300,462, price is now ￥260,348 per person
￥260,348
per person
Nov 17 - Nov 20
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,962 reviews)
A wonderful place with a fascinating history.
Reviewed on Sep 24, 2025
Hyatt Regency Chicago
Downtown Chicago
Price was ￥219,386, price is now ￥190,997 per person
￥190,997
per person
Nov 1 - Nov 4
found 5 hours ago
Roundtrip non-stop flight included
Komatsu (KMQ) to Chicago (ORD)
9.2/10 Wonderful! (3,346 reviews)
Our stay at the Hyatt Regency Chicago was absolutely amazing! The hotel was spotless, and the cleanliness throughout really stood out. Every staff member we encountered was professional, friendly, and went out of their way to make us feel welcome.
We loved the convenience of having plenty of on-site food options, which made it easy to grab a quick bite or sit down for a nice meal without leaving the property. The location couldn’t be better—just steps away from the Magnificent Mile and close to so many of Chicago’s top tourist attractions.
Overall, the Hyatt Regency Chicago exceeded our expectations, and we’ll definitely stay here again on our next trip!
Reviewed on Sep 23, 2025
4 Night Kid friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Downtown Chicago
Price was ￥272,392, price is now ￥228,168 per person
￥228,168
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,962 reviews)
A wonderful place with a fascinating history.
Reviewed on Sep 24, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Price was ￥286,338, price is now ￥240,816 per person
￥240,816
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (3,910 reviews)
Great super clean hotel . Amazing location close to everything.
Reviewed on Sep 24, 2025
Top Kid friendly Chicago Hotels
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
511 North Columbus Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,724 reviews)
"We came to Chicago for a Cubs game and a concert and loved the hotel. Would definitely recommend it."
Reviewed on Sep 17, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,979 reviews)
Palmer Palac
"This is one of the most beautiful hotels we have been to. We are a frequent couple traveling all over the world. We better call it a museum hotel. Lots of history and amazing decorations."
Reviewed on Sep 22, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,979 reviews)
"We stayed for two nights. The staff was friendly and courteous. The hotel is not brand new, but it is nice and clean."
Reviewed on Sep 22, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
