Historic Route 66 Vacations from ￥337,268
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The Latest Historic Route 66 Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥395,386, price is now ￥337,268 per person
￥337,268
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Breakfast was delish! Staff was nice..great location.
Reviewed on Mar 31, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥454,488, price is now ￥361,036 per person
￥361,036
per person
May 1 - May 6
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Amazing experience will be back soon
Reviewed on Mar 29, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥491,402, price is now ￥394,486 per person
￥394,486
per person
Jun 4 - Jun 8
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
My husband and I stayed in the presidential suite. It was absolutely spectacular. Wonderful food at prime Ocean and good breakfast. Amenities were out of this world. Customer service was amazing. We met the best bartender ever at the rooftop bar. The views were the best in Chicago!! highly recommend this hotel.
Reviewed on Mar 31, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥513,756, price is now ￥438,043 per person
￥438,043
per person
May 13 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Quality staff and the property was well appointed
Reviewed on Mar 30, 2026
Find the Best Historic Route 66 Vacation Packages
Historic Route 66 Hotel Deals
Central Loop Hotel
111 West Adams Street Chicago IL
The price is ￥17,419 per night from Apr 1 to Apr 2
￥17,419
￥20,447 total
Apr 1 - Apr 2
includes taxes & fees
8.6/10 Excellent! (2,051 reviews)
Great service, perfect location
Reviewed on Mar 31, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥18,553 per night from Apr 5 to Apr 6
￥18,553
￥21,779 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (10,028 reviews)
very old and grand hotel. felt like i was in the titanic but a hotel. Was very eerie and felt haunted. if you are in to ghost wonderful place to stay. the stairs alone are just breath taking.
Reviewed on Mar 31, 2026
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,907 per night from Apr 12 to Apr 13
￥21,907
￥25,717 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (4,031 reviews)
There is NO AIR CONDITIONING in any room NONE then they ran out of fans! Expedia advertises it does have air conditioning. Don’t stay here!
Reviewed on Mar 30, 2026
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.
