
Historic Route 66 Vacations from $244
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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
Price was $438, price is now $244 per person
$244
per person
Sep 3 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,663 reviews)
The employees were nice, friendly and helpful. The room was roomy, clean and the bed was nice and comfortable. I really like that the B&B Theater was right across the street to walk to. We enjoyed a movie at the Theater.
Reviewed on Jul 1, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,603, price is now $963 per person
$963
per person
Sep 15 - Sep 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.
Reviewed on Jul 1, 2026

Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $3,930, price is now $2,384 per person
$2,384
per person
Sep 15 - Sep 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
The staff was extremely friendly and flexible regarding scheduling; this place is amazing.
Reviewed on Jul 1, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,608, price is now $981 per person
$981
per person
Sep 15 - Sep 19
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
The male receptionist was extremely helpful, friendly, and welcoming. Unfortunately, the female receptionist was not as helpful or friendly. Her coworker noticed that I wasn't receiving the assistance I needed and stepped in to help, which I really appreciated.
I've stayed at several RIU hotels before and have always been able to check in early when a room was available. This was the first time I've experienced a significant delay with check-in.
Overall, I had a great stay. The hotel is in an excellent location, with everything within walking distance, making it very convenient to explore the area.
Breakfast is included, which is a nice benefit, but the quality could be improved. The selection was very basic and limited compared to what I've experienced at other RIU hotels.
Reviewed on Jul 2, 2026

Lodge Geneva National
Save 100% on your flight
Price was $1,083, price is now $696 per person
$696
per person
Sep 25 - Sep 29
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,375 reviews)
The Lodge is still under renovations. Our room was missing things like a headboard and bedside tables. The water pressure was weak. The amenities were nice for a family stay. It might be great once it’s all done. I wish we knew before booking.
Reviewed on Jun 27, 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
$76 nightly
The price is $89 total per night from Jul 9 to Jul 10
$89 total
Jul 9 - Jul 10
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
"Clean room :)"
Reviewed on Jun 28, 2026

The L Motel - Downtown Flagstaff
121 S. Milton Rd Flagstaff AZ
Fully refundableReserve now, pay when you stay
$44 nightly
The price is $49 total per night from Jul 6 to Jul 7
$49 total
Jul 6 - Jul 7
Total with taxes and fees
7.4/10 Good! (269 reviews)
"unsanitary sketchy poor english false advertisement of website looking nice overrated and priced"
Reviewed on Jul 1, 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
The price is $70 total per night from Jul 11 to Jul 12
$70 total
Jul 11 - Jul 12
Total with taxes and fees
8.6/10 Excellent! (718 reviews)
"Even though request when booking wasnt relayed, the manager was very helpful to accommodate my needs. Worked with me to help with late check out do to basic graduation. Clean room, quiet. All around great choice to stay at."
Reviewed on Jun 30, 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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