Historic Route 66 Vacation Packages 2026 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

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

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

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

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

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

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

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

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

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.