Historic Route 66 Vacations from $340

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

Save 100% on your flight
$340
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,676 reviews)
10/10 experience, will be back!

Reviewed on Aug 21, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$885
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Incredible hotel — it was clean, the room was spacious, the staff were incredibly friendly, and it was conveniently located in the heart of downtown, within walking distance of everything we needed.

Reviewed on Aug 21, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$724
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (518 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$1,101
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Excellent front desk staff. Great place, very clean with a touch of everyday luxury. Highly recommend!

Reviewed on Aug 21, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
Save 100% on your flight
$966
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
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Historic Route 66 Hotel Deals

Ramada by Wyndham Williams/Grand Canyon Area

Ramada by Wyndham Williams/Grand Canyon Area

950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
$59 nightly
$69 total
Aug 30 - Aug 31
Total with taxes and fees
Ramada by Wyndham Williams/Grand Canyon Area
Quality Inn Holbrook near Petrified Forest

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
$95 nightly
$111 total
Aug 23 - Aug 24
Total with taxes and fees
8.8/10 Excellent! (796 reviews)
"Always a decent overnight stay!!"

Reviewed on Aug 21, 2026

Quality Inn Holbrook near Petrified Forest
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood

Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood

14125 Hwy Z, I-44 and Hwy 28 Exit 163 St. Robert MO
Fully refundableReserve now, pay when you stay
$64 nightly
$70 total
Sep 5 - Sep 6
Total with taxes and fees
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood
See all 20,001 properties in Historic Route 66
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

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Currency
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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.