Historic Route 66 Vacations from $319

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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

$319
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)
We have stayed at Wildwood several times in the course of a decade, and it has been consistently reliable place to stay as a family. Rooms are clean and decent in size, and staff is friendly and polite. Breakfast is just okay - it is not something I would stay to enjoy. We parked on the street on this occasion and somewhat regretted it. It's a safe place, but it rained overnight, and somehow the car got dirtier. Outside maintenance (plants, etc) has not been kept up, and garden looks sad - but Missourian August has been brutally hot this year. It's a safe place to park on the street, but parking garage is convenient and free; it is where police parks as well. Next time we will use the garage.

Reviewed on Aug 14, 2026

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

Downtown Chicago
$372
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (2,711 reviews)
Wish we had a fridge and better outlets to charge phones

Reviewed on Aug 14, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$830
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The rooms were super clean and the staff was very friendly and welcoming. Will definitely consider staying again the next time I visit Chicago.

Reviewed on Aug 14, 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
$1,683
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
$797
per person
Oct 14 - Oct 18
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

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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
$62 nightly
$73 total
Aug 25 - Aug 26
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
"clean..nice room.good value"

Reviewed on Aug 14, 2026

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 31 - Sep 1
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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