Chicago Kid friendly Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 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 flight + Kid friendly hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
per person
15 Aug - 18 Aug
found 6 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,840 reviews)
Amazing Stay & Great Customer Service!
We had such a great experience at Silver Smith Hotel. The staff was welcoming and accommodating from the moment we arrived. We got there earlier than expected, around 1 p.m., and the hotel manager was kind enough to let us check in early so we didn’t have to wait around with our luggage until the usual 4 p.m. check-in. That was a huge help after traveling!
At checkout, they also held our bags for us, which made it super convenient since our flight wasn’t until later that afternoon. The customer service overall was excellent. We also loved the vouchers they provided, which could be used for drinks or food at their on-site restaurant — definitely a nice bonus during our stay.
I would absolutely recommend this hotel to anyone looking for a comfortable stay with great hospitality.
Reviewed on 4 Jul. 2025
Embassy Suites by Hilton Chicago North Shore Deerfield
per person
15 Aug - 18 Aug
found 6 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,261 reviews)
Honestly, the staff at this place were nothing short of amazing. The rooms were clean and the breakfast was great too! Overall a good quality stay. Will def be staying again.
Reviewed on 1 Jul. 2025
DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
per person
15 Aug - 18 Aug
found 6 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,881 reviews)
Perfect location, in two blocks the beach, in the opposite direction Michigan Ave.
Reviewed on 4 Jul. 2025
4 Night Kid friendly holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
per person
15 Aug - 18 Aug
found 6 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,840 reviews)
Amazing Stay & Great Customer Service!
We had such a great experience at Silver Smith Hotel. The staff was welcoming and accommodating from the moment we arrived. We got there earlier than expected, around 1 p.m., and the hotel manager was kind enough to let us check in early so we didn’t have to wait around with our luggage until the usual 4 p.m. check-in. That was a huge help after traveling!
At checkout, they also held our bags for us, which made it super convenient since our flight wasn’t until later that afternoon. The customer service overall was excellent. We also loved the vouchers they provided, which could be used for drinks or food at their on-site restaurant — definitely a nice bonus during our stay.
I would absolutely recommend this hotel to anyone looking for a comfortable stay with great hospitality.
Reviewed on 4 Jul. 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! (2,708 reviews)
"The hotel was very nice. We really liked our room and the view. The bed was very comfortable. We were disappointed that they had to turn the water off at night and the pool was closed for repairs."
Reviewed on 2 Jul. 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! (1,773 reviews)
"beautiful hotel, friendly and helpful staff."
Reviewed on 2 Jul. 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! (4,342 reviews)
"Great staff, food, and area!"
Reviewed on 4 Jul. 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.