Historic Route 66 Vacation Packages 2026 from $323

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$323

per person

Sep 27 - Sep 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,899 reviews)

in peak summer season they were having some major renovations that were incredibly loud all day long while trying to work and taking all the elevators and hallway space really couldn’t have been any more inconvenient i’m

Reviewed on Aug 15, 2026

The Wildwood Hotel

$349

per person

Sep 30 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to St. Louis (STL)

9.2/10 Wonderful! (1,676 reviews)

It was nice, it didn't smell when walking in. Breakfast was mid... not hot items like meat or anything ... you can make your own waffles tho so that was cool.

Reviewed on Aug 15, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$545

per person

Sep 27 - Sep 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

not enough to do no more eating hours

Reviewed on Aug 16, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$517

per person

Sep 27 - Sep 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,537 reviews)

We always enjoy our stay at the Swissotel!

Reviewed on Aug 16, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$595

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay. Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that. Overall a great spot. Affordable and lots of space with great views!

Reviewed on Aug 15, 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

$62 nightly

$73 total

Sep 7 - Sep 8

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

8.8/10 Excellent! (790 reviews)

"We needed a place to sleep on our trip back to Texas. We pulled in late. The lot was full. Very safe and clean. An older town and property but felt clean and had a lovely staff. Next morning we were the only car in lot at 8 am. Had breakfast and a coffee in the common area, which was also bright ..."

Reviewed on Aug 15, 2026

The L Motel - Downtown Flagstaff

121 S. Milton Rd Flagstaff AZ

Fully refundableReserve now, pay when you stay

$51 nightly

$57 total

Aug 17 - Aug 18

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.