Historic Route 66 Vacation Packages 2026 from $231

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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

$231

per person

Nov 25 - Nov 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to St. Louis (STL)

9.2/10 Wonderful! (1,672 reviews)

Would of been great if the fire alarm didn’t malfunction at 4:30am and the ran out of breakfast items

Reviewed on Sep 25, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$976

per person

Nov 28 - Dec 4

found 18 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (573 reviews)

We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.

Reviewed on Sep 26, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$867

per person

Nov 28 - Dec 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (2,025 reviews)

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$621

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (527 reviews)

Amazing stay for a family of four. The kids loved the pool, and the adults loved the hot tub! It felt close to the action, without being too close. Quiet but walkable to Navy Pier, Michigan Avenue, etc. Nearby multiple grocery stores. The building was well maintained and the neighborhood felt safe. The views from the room were unbelievable (the pictures don't do them justice). I would definitely stay here again.

Reviewed on Sep 26, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$664

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Breakfast, clean room, Staff

Reviewed on Sep 27, 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

$57 nightly

$67 total

Oct 27 - Oct 28

Total with taxes and fees

7.8/10 Good! (1,005 reviews)

"Easy in and off to the i 40"

Reviewed on Sep 26, 2026

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ

Fully refundableReserve now, pay when you stay

$86 nightly

$100 total

Oct 4 - Oct 5

Total with taxes and fees

8.8/10 Excellent! (832 reviews)

"Clean and spacious room!"

Reviewed on Sep 27, 2026

The L Motel - Downtown Flagstaff

121 S. Milton Rd Flagstaff AZ

Fully refundableReserve now, pay when you stay

$44 nightly

$49 total

Sep 28 - Sep 29

Total with taxes and fees

7.4/10 Good! (338 reviews)

"It was okay for the space needed TVs didn’t witk"

Reviewed on Sep 26, 2026

See all 20,191 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.