Historic Route 66 Vacation Packages 2026 from $340

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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

Save 100% on your flight

$340

per person

Sep 27 - Oct 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to St. Louis (STL)

9.2/10 Wonderful! (1,676 reviews)

10/10 experience, will be back!

Reviewed on Aug 21, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$885

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Incredible hotel — it was clean, the room was spacious, the staff were incredibly friendly, and it was conveniently located in the heart of downtown, within walking distance of everything we needed.

Reviewed on Aug 21, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$724

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (518 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$1,101

per person

Oct 27 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (550 reviews)

Excellent front desk staff. Great place, very clean with a touch of everyday luxury. Highly recommend!

Reviewed on Aug 21, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$966

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,638 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

$59 nightly

$69 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

$95 nightly

$111 total

Aug 23 - Aug 24

Total with taxes and fees

8.8/10 Excellent! (796 reviews)

"Always a decent overnight stay!!"

Reviewed on Aug 21, 2026

Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood

14125 Hwy Z, I-44 and Hwy 28 Exit 163 St. Robert MO

Fully refundableReserve now, pay when you stay

$64 nightly

$70 total

Sep 5 - Sep 6

Total with taxes and fees

See all 20,001 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.