Historic Route 66 Luxury Vacations

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Top Luxury vacation packages in Historic Route 66

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

Pendry Chicago

Downtown Chicago
¥337,640
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,160 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥492,738
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥507,324
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,853 reviews)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥454,382
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥420,638
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,960 reviews)
Great location but the rooms are small and outdated

Reviewed on Sep 1, 2026

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5* Luxury vacations in Historic Route 66

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥359,054
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥425,980
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,018 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥490,370
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,013 reviews)
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3 Night Luxury vacations in Historic Route 66

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥303,014
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥328,339
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
¥337,640
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,160 reviews)
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4 Night Luxury vacations in Historic Route 66

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
¥353,818
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥372,235
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥425,980
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,018 reviews)
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.