
Historic Route 66 Vacations from ¥218,942
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The Latest Historic Route 66 Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
The cleanliness of the hallways in the hotel and on the pier was exceptional. The views of the water and downtown lights were the best and all the eating places on the pier were excellent choices to choose from.
Reviewed on Aug 13, 2025




LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Being right on the river with great views made this even better! Close to everything & friendly, helpful staff
Reviewed on Aug 13, 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 refundable
The price is ¥10,072 per night from Sep 14 to Sep 15
¥10,072
¥11,823 total
Sep 14 - Sep 15
includes taxes & fees
8.6/10 Excellent! (3,351 reviews)
"Lovely compact hotel"
Reviewed on Aug 11, 2025

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥19,840 per night from Sep 1 to Sep 2
¥19,840
¥23,291 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,982 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"
Reviewed on Aug 14, 2025

The Aquarius Casino Resort, BW Premier Collection
1900 S Casino Dr, Laughlin, NV
Fully refundableReserve now, pay when you stay
The price is ¥5,007 per night from Aug 18 to Aug 19
¥5,007
¥9,444 total
Aug 18 - Aug 19
includes taxes & fees
8/10 Very Good! (6,803 reviews)
"I enjoyed our stay"
Reviewed on Aug 13, 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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