
Far North Side Kid friendly Vacations
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Top Kid friendly vacation packages in Far North Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥238,023, price is now ¥192,498 per person
¥192,498
per person
Apr 15 - Apr 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all
Reviewed on Feb 2, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥286,713, price is now ¥240,126 per person
¥240,126
per person
Apr 15 - Apr 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026

Pendry Chicago
Downtown Chicago
Price was ¥235,598, price is now ¥198,214 per person
¥198,214
per person
Apr 15 - Apr 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.
Reviewed on Jan 31, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥301,802, price is now ¥255,608 per person
¥255,608
per person
Apr 15 - Apr 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

The Emily Hotel
Downtown Chicago
Price was ¥241,574, price is now ¥208,057 per person
¥208,057
per person
Apr 15 - Apr 18
found 24 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again.
Reviewed on Jan 25, 2026
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View all trips5* Kid friendly vacations in Far North Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥286,713, price is now ¥240,126 per person
¥240,126
per person
Apr 15 - Apr 18
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥301,802, price is now ¥255,608 per person