Historic Route 66 Vacation Packages 2026 from $308

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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

$308

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7.6/10 Good! (2,711 reviews)

It’s a nice clean room …Has all the essentials and it’s in downtown….what mush can a guy asked for

Reviewed on Aug 14, 2026

The Wildwood Hotel

Save 100% on your flight

$308

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

Level Chicago Fulton Market

Downtown Chicago

$1,022

per person

Oct 27 - Nov 3

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$654

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)

Rooftop was amazing! Inside bar was great, too!

Reviewed on Aug 14, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$742

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,537 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

$62 nightly

$73 total

Aug 30 - Aug 31

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 25 - Aug 26

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.