
Historic Route 66 Kid friendly Vacations
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Top Kid friendly vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥580,096, price is now ¥458,780 per person
¥458,780
per person
Jul 30 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,506 reviews)
At midnight there was a ceiling leak in the bathroom. Although the staff member that helped us was very thoughtful and helpful, there was neither an apology or compensation from the hotel itself which one would expect after everything we had on the bathroom counter was soaked and having to pack up everything at one in the morning to switch rooms.
Reviewed on May 8, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥721,214, price is now ¥474,336 per person
¥474,336
per person
Jul 30 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Beautiful hotel, very impressed with the cleanliness, space in the room and the breakfast. So pleased we chose this hotel as the location was excellent 👌
Reviewed on May 7, 2026

Swissotel - Chicago
Downtown Chicago
Price was ¥701,022, price is now ¥484,821 per person
¥484,821
per person
Jul 30 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close.
The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.
Reviewed on May 6, 2026

Sentral Michigan Avenue
Downtown Chicago
Price was ¥728,058, price is now ¥583,316 per person
¥583,316
per person
Jul 30 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,142 reviews)
The one issue I had with the property was the couch had visible stains. I would recommend having the couch replaced.
Reviewed on May 1, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥918,453, price is now ¥742,610 per person
¥742,610
per person
Jul 30 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The staff was very welcoming and the rooms were super clean & well maintained.
The location is also very convenient, quiet but close and walking distance to the river and the amazing restaurants. Will definitely revisit the Penninsula soon.
Reviewed on May 2, 2026
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View all trips5* Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

The Peninsula Chicago
Downtown Chicago
Price was ¥918,453, price is now ¥742,610 per person
¥742,610
per person
Jul 30 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The staff was very welcoming and the rooms were super clean & well maintained.
The location is also very convenient, quiet but close and walking distance to the river and the amazing restaurants. Will definitely revisit the Penninsula soon.
Reviewed on May 2, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
