West Side Kid friendly Vacations

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5* Kid friendly vacations in West Side

Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥417,428
per person
Sep 17 - Sep 20
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Nobu Hotel Chicago

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

Waldorf Astoria Chicago

Waldorf Astoria Chicago

Downtown Chicago
¥672,486
per person
Oct 7 - Oct 11
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
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4 Night Kid friendly vacations in West Side

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

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

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥429,498
per person
Oct 7 - Oct 11
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Silversmith Hotel Chicago Downtown

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

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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

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