Chicago Kid friendly Vacations
Book a Kid friendly Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Kid friendly vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
Price was ￥134,631, price is now ￥124,475 per person
￥124,475
per person
May 5 - May 7
found 11 hours ago
Roundtrip flight included
St. Louis (STL) to Chicago (ORD)
8.2/10 Very Good! (2,811 reviews)
Stephanie was so Fantastic she was very understanding made the check in process incredibly fast. I loved the location plenty of things to do bowling, movies, dinner, Navey Pier, etc. One of the best experiences every the room was Awesome!!!
Reviewed on Feb 27, 2026
Radisson Blu Aqua Hotel Chicago
Downtown Chicago
Price was ￥441,868, price is now ￥413,739 per person
￥413,739
per person
Apr 15 - Apr 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,861 reviews)
Clean, modern rooms and aesthetic. Pool was great for kids.
Reviewed on Mar 1, 2026
3 Night Kid friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago
Downtown Chicago
Price was ￥233,878, price is now ￥223,562 per person
￥223,562
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,972 reviews)
The room was not what we expected based on the pictures from the website. The room completely lacked any personality or comfort. There was only one towel in the room for the two of us, so I had to dry off from my shower with hand towels. The room was awkwardly arranged with two very uncomfortable chairs and no real sitting arrangement (as the word "suite" should indicate), and the television is inconveniently small for the location in the room as it was placed on the far wall from the bed in a very long and narrow room. Even sitting in the room to relax and have a pre-evening drink was difficult as there are no tables upon which to put a drink, even if you wanted to sit in the very uncomfortable chairs. Additionally, the room was either dark or overwhelmingly bright, with not a lot of balance and felt as welcoming as a drive up motel room.
The staff was gracious and helpful. The bar is a nice feature but with an uncomfortable room that didn't invite a feeling of welcome, the overall stay was very disappointing. We have stayed in the hotel before and was excited to return. This trip was such a disappointment.
Reviewed on Feb 28, 2026
Hilton Chicago
Downtown Chicago
Price was ￥263,328, price is now ￥242,344 per person
￥242,344
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,655 reviews)
Hotel was really nice and super clean. Staff were amazing.
Reviewed on Mar 3, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
Price was ￥255,964, price is now ￥247,260 per person
￥247,260
per person
Apr 14 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,811 reviews)
Stephanie was so Fantastic she was very understanding made the check in process incredibly fast. I loved the location plenty of things to do bowling, movies, dinner, Navey Pier, etc. One of the best experiences every the room was Awesome!!!
Reviewed on Feb 27, 2026
4 Night Kid friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Price was ￥413,136, price is now ￥374,802 per person
￥374,802
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Izumo (IZO) to Chicago (ORD)
8.6/10 Excellent! (4,372 reviews)
Sam at the front desk was very helpful.The hotel was great in a great location.I would stay again
Reviewed on Mar 4, 2026
Hilton Chicago
Downtown Chicago
Price was ￥421,418, price is now ￥390,586 per person
￥390,586
per person
Apr 15 - Apr 19
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,655 reviews)
Hotel was really nice and super clean. Staff were amazing.
Reviewed on Mar 3, 2026
Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
Price was ￥405,252, price is now ￥376,924 per person
￥376,924
per person
May 1 - May 5
found 1 day ago
Roundtrip flight included
Izumo (IZO) to Chicago (ORD)
8.8/10 Excellent! (1,197 reviews)
This location was fantastic! Right in the middle of everything we wanted to see in Chicago.
Reviewed on Mar 2, 2026
Top Kid friendly Chicago Hotels
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
511 North Columbus Drive Chicago IL
Book a stay at this 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! (2,816 reviews)
The bed has long hairs left behind and they could not get the garage situation easy to exit or enter and never said the “drink cards” were for certain times just not a comfortable stay!
Reviewed on Mar 3, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,313 reviews)
Good stay! Great staff!
Reviewed on Mar 4, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,715 reviews)
Old property bad food long lines
Reviewed on Mar 5, 2026
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.
