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.
The Wildwood Hotel

The Wildwood Hotel

Save 100% on your flight
$406
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,657 reviews)
Friendly staff. Building is very run down. Paint in rooms pealing. Tiles in bathroom have years of buildup. Sheets were very cheap. Pillows were cheap. AC was loud, with broken parts.

Reviewed on Sep 5, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$744
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
The hotel was so amazing for us. Staff was accommodating and helped us immensely. The restaurant for breakfast and the roof top wil keep you coming back. We will try to stay there as much as we can while in Chicago.. Lester and Luis at the restaurants need a bonus. They kept the breakfast crowd well organized.

Reviewed on Sep 4, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
$1,147
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

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$911
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$607
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Cute hotel in great location..make sure to ask for a street side room or your view will be a brick wall and the room will be like a dark cave. 😭

Reviewed on Sep 4, 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
$64 nightly
$75 total
Sep 13 - Sep 14
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
$88 nightly
$103 total
Oct 4 - Oct 5
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
$46 nightly
$51 total
Sep 7 - Sep 8
Total with taxes and fees
7.4/10 Good! (315 reviews)
"Good 3 beds Family room"

Reviewed on Sep 5, 2026

The L Motel - Downtown Flagstaff
See all 20,007 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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