Historic Route 66 Vacations from $339
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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
$737
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$717
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.
Reviewed on Aug 17, 2026
Swissotel - Chicago
Downtown Chicago
$574
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.
Reviewed on Aug 17, 2026
Level Chicago – Old Town
Downtown Chicago
$554
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
The property seems new and well kept. There are many amenities that enhance the stay including a pool, hot tub, basketball ball court, game room, sauna and steam room. We loved our stay.
Only negatives were there was not an ice machine, there was not daily cleaning service, the towels were OK and we needed our trash emptied but were many sure how to request that.
Overall a great spot. Affordable and lots of space with great views!
Reviewed on Aug 15, 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
$62 nightly
$73 total
Aug 23 - Aug 24
Total with taxes and fees
Quality Inn Holbrook near Petrified Forest
2602 Navajo Blvd Holbrook AZ
Fully refundableReserve now, pay when you stay
$93 nightly
$108 total
Sep 6 - Sep 7
Total with taxes and fees
8.8/10 Excellent! (790 reviews)
"We needed a place to sleep on our trip back to Texas. We pulled in late. The lot was full. Very safe and clean. An older town and property but felt clean and had a lovely staff. Next morning we were the only car in lot at 8 am. Had breakfast and a coffee in the common area, which was also bright ..."
Reviewed on Aug 15, 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
8.6/10 Excellent! (740 reviews)
"We stayed here first while at my son’s Graduation. We didn’t get much sleep, there was a couple drunk guys on the balcony at 1 Am cussing and fight and yelling. Slamming doors and being awful, we didn’t approach or leave the room because we heard a guy say if it wasn’t for me your drunk ass wouldn’t ..."
Reviewed on Aug 16, 2026
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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