Historic Route 66 Vacation Packages 2026 from $385

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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

$385

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to St. Louis (STL)

9.2/10 Wonderful! (1,672 reviews)

We were there for three days. Every single person was helpful. The only downside for us was the lack of choices for the breakfast. After the first day, we went out to breakfast at other locations.

Reviewed on Oct 2, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$731

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,340 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$561

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$536

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,003 reviews)

We had such a great experience at Harrah’s Casino & Hotel! We stayed for one night to celebrate my birthday, and everything was wonderful from start to finish. Our room was nice, clean, and comfortable, and the staff was absolutely amazing—everyone we interacted with was so friendly and welcoming. The casino was a lot of fun, and we also had lunch at Cross Street Grill. The food was delicious, the prices were great, and it was such a convenient option right on site. Overall, we had an amazing birthday getaway and would definitely recommend Harrah’s to anyone looking for a fun and relaxing trip. We’re already talking about planning our next visit!

Reviewed on Sep 29, 2026

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$480

per person

Nov 4 - Nov 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (1,120 reviews)

Good location and parking, but the room has poor soundproofing, we can here the noise from outside

Reviewed on Oct 2, 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

$49 nightly

$58 total

Nov 2 - Nov 3

Total with taxes and fees

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ

Fully refundableReserve now, pay when you stay

$86 nightly

$100 total

Oct 18 - Oct 19

Total with taxes and fees

The L Motel - Downtown Flagstaff

121 S. Milton Rd Flagstaff AZ

Fully refundableReserve now, pay when you stay

$40 nightly

$45 total

Nov 2 - Nov 3

Total with taxes and fees

See all 20,234 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.