Historic Route 66 Vacations from $294

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

Downtown Chicago
Save 100% on your flight
$294
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (2,711 reviews)
Great location! Would 100% recommend 👌

Reviewed on Aug 13, 2026

The Wildwood Hotel

The Wildwood Hotel

Save 100% on your flight
$311
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,676 reviews)
Great property

Reviewed on Aug 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$665
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$735
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on Aug 12, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$609
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Clean well maintained hotel. Staff were helpful.

Reviewed on Aug 14, 2026

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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
$63 nightly
$74 total
Aug 20 - Aug 21
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
$93 nightly
$108 total
Sep 6 - Sep 7
Total with taxes and fees
Quality Inn Holbrook near Petrified Forest
The L Motel - Downtown Flagstaff

The L Motel - Downtown Flagstaff

121 S. Milton Rd Flagstaff AZ
Fully refundableReserve now, pay when you stay
$56 nightly
$62 total
Aug 19 - Aug 20
Total with taxes and fees
The L Motel - Downtown Flagstaff
See all 19,875 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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English
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.