Historic Route 66 Vacation Packages 2026 from $363

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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

$363

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to St. Louis (STL)

9.2/10 Wonderful! (1,672 reviews)

This place is great and so are the staff. I would not expect a place this nice to allow pets.

Reviewed on Aug 8, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$744

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

Great staff, great place!

Reviewed on Aug 5, 2026

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$2,857

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,004 reviews)

Remodeled and Inviting Free EV

Save 100% on your flight

$551

per person

Sep 27 - Oct 2

found 23 hours ago

Roundtrip flight included

Atlanta (ATL) to St. Louis (STL)

10/10 Exceptional! (1 review)

It was nice to stay for a weekend but the neighborhood was nice I like the location where it wasn't too far from grocery stores food areas the only thing I was saying is it's nothing for the kids to do but overall I like it

Reviewed on Aug 7, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$900

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,512 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 17 - Aug 18

Total with taxes and fees

7.8/10 Good! (1,008 reviews)

"I was surprise when I was not asked for ID when I said I'd lost my key."

Reviewed on Aug 8, 2026

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ

Fully refundableReserve now, pay when you stay

$87 nightly

$102 total

Sep 6 - Sep 7

Total with taxes and fees

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 19,952 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.