Historic Route 66 Vacations from ￥144,473
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The Latest Historic Route 66 Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥177,800, price is now ￥144,473 per person
￥144,473
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Jasmine was courteous and friendly, made our check in process smooth. Clean rooms and the breakfast was amazing. I definitely recommend staying here.
Reviewed on Dec 31, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥309,426, price is now ￥242,644 per person
￥242,644
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.
Reviewed on Dec 29, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥179,608, price is now ￥144,876 per person
￥144,876
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥193,070, price is now ￥157,083 per person
￥157,083
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The only downfall here was the valet parking. They give you a ticket to call ahead but then you get to the front and THEN they have someone go get a car 15+ minutes away. Some days only one kid is working and has multiple cars to get and bring back. Obviously not his fault! But the process needs tweaking and is frustrating. Also, wouldn’t necessarily recommend for a family with small kids. But it did what it needed to for our stay.
Reviewed on Dec 30, 2025
Find the Best Historic Route 66 Vacation Packages
Historic Route 66 Hotel Deals
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥12,718 per night from Jan 12 to Jan 13
￥12,718
￥14,930 total
Jan 12 - Jan 13, 2026
includes taxes & fees
8.6/10 Excellent! (3,329 reviews)
Nice hotel, just wish it was bigger. But nice! Great location
Reviewed on Dec 26, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,941 per night from Jan 6 to Jan 7
￥13,941
￥16,365 total
Jan 6 - Jan 7, 2026
includes taxes & fees
8.8/10 Excellent! (3,613 reviews)
Clean room , great location.
Reviewed on Dec 30, 2025
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥19,056 per night from Jan 6 to Jan 7
￥19,056
￥26,948 total
Jan 6 - Jan 7, 2026
includes taxes & fees
8.4/10 Very Good! (2,424 reviews)
Overall very clean and very friendly staff
Reviewed on Dec 28, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.
