Historic Route 66 Vacation Packages 2026 from $308

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Historic Route 66 vacation packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$308

per person

Dec 9 - Dec 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (3,084 reviews)

The Wildwood Hotel

$349

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to St. Louis (STL)

9.2/10 Wonderful! (1,679 reviews)

The staff are super helpful, friendly and professional. The room was very comfortable and quiet. Some of the furnishings are overdue for replacement (chairs with worn out upholstery) but nothing terrible. Overall wonderful stay and will definitely return to next time I am in this area.

Reviewed on Oct 3, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$860

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,340 reviews)

The staff were friendly. The location, hotel decor, and amenities were nice. The breakfast was decent and the blankets were thin but we enjoyed our stay.

Reviewed on Oct 3, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$605

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$472

per person

Dec 12 - Dec 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Historic Route 66

View all trips

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

$49 nightly

$58 total

Nov 2 - Nov 3

Total with taxes and fees

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ

Fully refundableReserve now, pay when you stay

$86 nightly

$100 total

Oct 18 - Oct 19

Total with taxes and fees

8.8/10 Excellent! (844 reviews)

"We stayed one night at the Quality Inn. It was quiet and comfortable. The staff was very accommodating and polite. We used the ice machine several times and it worked well. I would recommend this Inn. We didn’t use the pool since it was chilly. We enjoyed the complimentary breakfast. The coffee was ..."

Reviewed on Oct 3, 2026

The L Motel - Downtown Flagstaff

121 S. Milton Rd Flagstaff AZ

Fully refundableReserve now, pay when you stay

$41 nightly

$45 total

Nov 3 - Nov 4

Total with taxes and fees

See all 20,234 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.