
West Side Kid friendly Vacations
Book a Kid friendly Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥109,000 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
- Rest easyPlan, book, and manage your trip all in one place
5* Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.


Nobu Hotel Chicago
Downtown Chicago
¥545,081
per person
Oct 7 - Oct 11
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
Rooms and beds are always so nice. Very calming and always get a good night’s sleep. I’ve always had a great experience. One detail which falls short is the toilet paper is very rough. Aside from this detail everything else surpasses my expectations.
Reviewed on Aug 16, 2026

4 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Fairmont Chicago at Millennium Park
Downtown Chicago
¥400,452
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Fairmont maybe an old hotel but it is well maintained hotel. With large rooms, great views of the skyline especially at night from our window. And Le Labo toiletries is a plus. Also Many great restaurants nearby
Reviewed on Aug 17, 2026


Silversmith Hotel Chicago Downtown
Downtown Chicago
¥424,789
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,311 reviews)
Hotel is the heart of downtown. Across the street from a solid breakfast spot and great proximity to the CTA. Went from downtown to Logan Square, Wicker Park, Lincoln Park, theater district, etc and never needed my car. Depending on the amount of luggage, park and ride via blue line from O’hare or somewhere outside downtown to save on parking is a good idea. Pets not allowed. But if no pets this is a great hotel for a Chicago trip,
Reviewed on Aug 17, 2026
Things to do

Chicago: Navy Pier Centennial Wheel Ticket
¥3,920
per adult
90% of travellers recommend

Chicago: Willis Tower Skydeck and The Ledge Ticket
¥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

