Historic Route 66 Vacations from $406
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
$1,137
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.
Reviewed on Sep 2, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$787
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
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View all tripsHistoric Route 66 Hotel Deals
Ramada by Wyndham Williams/Grand Canyon Area
950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
$64 nightly
$75 total
Sep 13 - Sep 14
Total with taxes and fees
Quality Inn Holbrook near Petrified Forest
2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
$88 nightly
$103 total
Oct 4 - Oct 5
Total with taxes and fees
The L Motel - Downtown Flagstaff
121 S. Milton Rd Flagstaff AZ
Fully refundableReserve now, pay when you stay
$46 nightly
$51 total
Sep 7 - Sep 8
Total with taxes and fees
7.4/10 Good! (314 reviews)
"Clean room in a convenient location. Wanted to check in an hour early (forgot about time change from Colorado), room was ready, but had to pay a $10 early check in fee. Room had two large beds with 1 side table between them. TV was mounted on the wall. There was a chair, refrigerator, and fold up ..."
Reviewed on Sep 3, 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.
Find the Best Historic Route 66 Vacation Packages
Historic Route 66 Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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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.
