Historic Route 66 Vacations from $340

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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

The Wildwood Hotel

Save 100% on your flight
$340
per person
Sep 27 - Oct 2
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 Fulton Market

Level Chicago Fulton Market

Downtown Chicago
$772
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

Westgate Branson Lakes Resort

Westgate Branson Lakes Resort

Save 100% on your flight
$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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$829
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
We were blown away that every single person associated with the hotel was kind, helpful, great at their job, accommodating, and basically wonderful. The hotel was amazingly clean, environmentally forward-thinking, safe, and handy to EVERYTHING in downtown Chicago. The best surprise was the massive breakfast buffet that was included in the price of the room. The breakfast accommodated a steady stream of guests and never ran out of the ample variety of food. It was the perfect way to begin each day. Another treat: the rooftop bar and the hotel bar. Excellent service and skilled bar-tenders. It's a gem and don't hesitate to book a room in this hotel.

Reviewed on Aug 19, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
Save 100% on your flight
$501
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,899 reviews)
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Historic Route 66 Hotel Deals

Ramada by Wyndham Williams/Grand Canyon Area

Ramada by Wyndham Williams/Grand Canyon Area

950 N Grand Canyon Blvd Williams AZ
Fully refundableReserve now, pay when you stay
$74 total
per night
Aug 26 - Aug 27
Ramada by Wyndham Williams/Grand Canyon Area
Quality Inn Holbrook near Petrified Forest

Quality Inn Holbrook near Petrified Forest

2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
$98 total
per night
Sep 17 - Sep 18
8.8/10 Excellent! (791 reviews)
"Comfortable bed. Great location."

Reviewed on Aug 19, 2026

Quality Inn Holbrook near Petrified Forest
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood

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
$70 total
per night
Sep 5 - Sep 6
Days Inn by Wyndham St. Robert Waynesville/Ft. Leonard Wood
See all 20,001 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.

Find the Best Historic Route 66 Vacation Packages

Historic Route 66 Essential Information

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