Chicago Kid friendly Vacations
Book a Kid friendly Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Kid friendly vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
found 3 hours ago
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
First time staying here. The staff were great and the hotel has a lot going on. The bed in my room was so comfortable for my short stay. Would stay again. Nice people work here and the security officers were pleasant as well.
.
Reviewed on Jul 19, 2025
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,718 reviews)
Hotel was nice. Walking distance to pretty much everything. Breakfast is very good and the evening reception. Will definitely book again and recommend
Reviewed on Jul 17, 2025
The Royal Sonesta Chicago Downtown
Downtown Chicago
per person
Sep 21 - Sep 24
found 3 hours ago
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (2,690 reviews)
3/5 the stay itself was fine, but the communication left a lot to be desired. I sent a message after checking out that I accidentally left my MacBook charger in the room not necessarily expecting to be returned, but just as a courtesy. Unfortunately, they never acknowledged the message, which came across as unprofessional and unhelpful. That lack of basic communication affected my overall stay.
Reviewed on Jul 19, 2025
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
per person
Sep 21 - Sep 24
found 3 hours ago
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
8.4/10 Very Good! (4,382 reviews)
Nice property in the midst of downtown. Easy to walk to different places (Starbucks, train station, corner store).
Reviewed on Jul 20, 2025
3 Night Kid friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Downtown Chicago
per person
Sep 21 - Sep 24
found 3 hours ago
Roundtrip non-stop flight included
Singapore (SIN) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
First time staying here. The staff were great and the hotel has a lot going on. The bed in my room was so comfortable for my short stay. Would stay again. Nice people work here and the security officers were pleasant as well.
.
Reviewed on Jul 19, 2025
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,718 reviews)
Hotel was nice. Walking distance to pretty much everything. Breakfast is very good and the evening reception. Will definitely book again and recommend
Reviewed on Jul 17, 2025
4 Night Kid friendly vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
per person
Sep 30 - Oct 4
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (4,382 reviews)
Nice property in the midst of downtown. Easy to walk to different places (Starbucks, train station, corner store).
Reviewed on Jul 20, 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! (2,716 reviews)
"Hotel was nice. Walking distance to pretty much everything. Breakfast is very good and the evening reception. Will definitely book again and recommend"
Reviewed on Jul 17, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,784 reviews)
"Beautiful historic hotel! Loved the live music in the lobby. I was there in a traditional room sith 2 double beds, and then i upgraded to a suite. Both were nice rooms, but i LOVE a good suite! Personnel at the hotel were kind and helpful. Have a cocktail and a brownie in the lobby- you won't regret ..."
Reviewed on Jul 15, 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! (4,490 reviews)
Great location for exploring the city!
"Great location. The breakfast and happy hour were really great and service during both was great. However, front desk service was always slow. There never seemed to be enough people working."
Reviewed on Jul 19, 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.