
Historic Route 66 Vacations from $308
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.


Level Chicago Fulton Market
Downtown Chicago
$818
per person
Oct 28 - Nov 3
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

The Wildwood Hotel
$370
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,676 reviews)
We were pleasantly surprised at how nice the facility was. A premium hotel at motel prices! Very near, walking distance in most cases, great restaurants, shopping and even a 10 plex cinema right across the street. We will stay here again!
Reviewed on Aug 19, 2026

Level Chicago – Old Town
Downtown Chicago
$638
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

Westgate Branson Lakes Resort
$592
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Springfield (SGF)
8.4/10 Very Good! (996 reviews)
Very nice, clean, and spacious rooms. Very nice property with lots to do and excellent view of the lake.
Reviewed on Aug 18, 2026
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Ramada by Wyndham Williams/Grand Canyon Area
950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
$58 nightly
$68 total
Sep 2 - Sep 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
Sep 6 - Sep 7
Total with taxes and fees
8.8/10 Excellent! (791 reviews)
"Comfortable bed. Great location."
Reviewed on Aug 19, 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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