Historic Route 66 Vacation Packages 2026 from $313

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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

$313

per person

Oct 22 - Oct 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7.6/10 Good! (2,721 reviews)

The Wildwood Hotel

Save 100% on your flight

$322

per person

Sep 24 - Sep 28

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

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 1 day 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

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$1,800

per person

Sep 13 - Sep 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (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 18 - Aug 19

Total with taxes and fees

7.8/10 Good! (1,009 reviews)

"Staff was nice, but they were hanging out at the restaurant for some time while we and others were waiting in the lobby."

Reviewed on Aug 9, 2026

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ

Fully refundableReserve now, pay when you stay

$89 nightly

$104 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

$64 nightly

$70 total

Sep 5 - Sep 6

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.