Historic Route 66 Vacation Packages 2026 from $454

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The Latest Historic Route 66 vacation packages

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

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$454

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (165 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$959

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

The Wildwood Hotel

Save 100% on your flight

$553

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to St. Louis (STL)

9.2/10 Wonderful! (1,657 reviews)

No room, reset or towels or trash pickup when staying two nights. 20mi from St Louis

Reviewed on Sep 19, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$738

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (520 reviews)

Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!

Reviewed on Sep 19, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$1,090

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

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Historic 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

$57 nightly

$67 total

Oct 20 - Oct 21

Total with taxes and fees

7.8/10 Good! (1,007 reviews)

"The place had bed bugs.would not recommended staying there."

Reviewed on Sep 19, 2026

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ

Fully refundableReserve now, pay when you stay

$86 nightly

$100 total

Oct 4 - Oct 5

Total with taxes and fees

8.8/10 Excellent! (824 reviews)

"At check-in we asked for a room downstairs as my husband has a rod through his foot and up his leg. He’s is not able to go up stairs. We were told that we could have a room downstairs with two queen beds. I said we did not need two beds. He said that’s all we have and it’s $13 more for the extra ..."

Reviewed on Sep 18, 2026

The L Motel - Downtown Flagstaff

121 S. Milton Rd Flagstaff AZ

Fully refundableReserve now, pay when you stay

$44 nightly

$49 total

Sep 21 - Sep 22

Total with taxes and fees

See all 20,180 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.