West Side Kid friendly Vacations

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Top Kid friendly vacation packages 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
￥285,926
per person
Sep 26 - Sep 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Amazing hotel, great location in the heart of it all.

Reviewed on Aug 15, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥543,686
per person
Nov 1 - Nov 7
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
￥500,735
per person
Nov 1 - Nov 7
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
It was a great place.

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
￥441,612
per person
Nov 1 - Nov 7
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Very clean room, great friendly staff.

Reviewed on Aug 15, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
￥413,212
per person
Nov 1 - Nov 7
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
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5* Kid friendly vacations in West Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥543,686
per person
Nov 1 - Nov 7
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
￥764,728
per person
Sep 18 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to West Side
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3 Night Kid friendly vacations in West Side

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
￥268,212
per person
Sep 26 - Sep 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Overall great experience

Reviewed on Aug 15, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥329,906
per person
Sep 26 - Sep 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
￥285,926
per person
Sep 26 - Sep 29
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Amazing hotel, great location in the heart of it all.

Reviewed on Aug 15, 2026

Don't see what you're looking for?
See all available trips from Tokyo to West Side
View all trips

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.