Historic Route 66 Vacations from $361
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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
$361
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)
This was a very nice property and had a great area for our dogs. The front desk lady was very nice and there were treats for our dogs. We will definitely stay here again when in the St. Louis area. The room was clean and decorated nicely. Two thumbs up!!
Reviewed on Aug 20, 2026
Level Chicago – Old Town
Downtown Chicago
$684
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on Aug 19, 2026
Level Chicago Fulton Market
Downtown Chicago
$782
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
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View all tripsHistoric 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
$59 nightly
$69 total
Aug 30 - Aug 31
Total with taxes and fees
Quality Inn Holbrook near Petrified Forest
2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
$95 nightly
$111 total
Aug 21 - Aug 22
Total with taxes and fees
8.8/10 Excellent! (792 reviews)
"Clean and comfortable."
Reviewed on Aug 20, 2026
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
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.
Find the Best Historic Route 66 Vacation Packages
Historic Route 66 Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
