Northwest Side Kid friendly Vacations

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Top Kid friendly vacation packages in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
¥379,826
per person
Oct 1 - Oct 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥405,665
per person
Oct 1 - Oct 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.

Reviewed on Aug 17, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥523,290
per person
Oct 1 - Oct 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on Aug 16, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥500,735
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

Downtown Chicago
¥393,084
per person
Oct 1 - Oct 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (4,495 reviews)
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5* Kid friendly vacations in Northwest 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 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥523,290
per person
Oct 1 - Oct 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on Aug 16, 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
¥582,604
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip flight included
Kitakyushu (KKJ) 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

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3 Night Kid friendly vacations in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥498,730
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
8.2/10 Very Good! (2,899 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥595,752
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.4/10 Exceptional! (2,311 reviews)
The staff especially Beverly and George were extremely welcoming and accommodating not just towards me but to other guests that I noticed. No beverage or snack vending machines on site but there is a Circle K a half block away. Walking distance to many sites and activities and safe to do so. Be prepared to hear the L roaring depending on your room location. Also, my 1st room that was assigned on the front side did not have a work table at all which I found odd and unusual (no place to eat in your room). That was unacceptable to me so they provided me with an interior room which was quiet but faced a brick building that was very close.

Reviewed on Aug 16, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥511,166
per person
Oct 9 - Oct 12
found 15 hours ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
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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 Northwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.