
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.


Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,268, price is now $730 per person
$730
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,371, price is now $859 per person
$859
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Our first time visiting Chicago and the hotel was hands down the best. Located in downtown Chicago, which made everything pretty much walking distance. The complimentary breakfast (buffet style) was great with many options to choose from. Staff were amazing and were kind enough to accommodate us with an early check- in (with an extra cost since we arrived in at 7:30am).
My one and only complaint was that it would have been nice to have our breakfast included with the early check in since we paid $100 for that. We were told that we were welcome to go have breakfast but at an additional cost which was $25/adult and $12/child. We paid it since we had just come in from a long flight and wanted some food. Overall a great experience, we definitely plan on staying again at our next trip to Chicago.
Reviewed on Jul 3, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,380, price is now $872 per person
$872
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
We had a wonderful stay! The hotel was very clean, and the staff who checked us in and out were incredibly kind and welcoming. The location was perfect—we were able to walk everywhere we wanted to go, which made our trip so convenient. I would definitely stay here again!
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 1 day 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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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! (1,000 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! (270 reviews)
"Looks can be deceiving, this place may look rough around the edges from the outside but for the best price and location in town this was exactly what I’m looking for and why I will highly consider it again when I come back to Flagstaff because it’s affordable and newly renovated"
Reviewed on Jul 2, 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! (719 reviews)
"The room itself was nice. Had reserved a room for accessibility issues and was given an upstairs room with steep stairs. Food from the previous visitor was left in the fridge. Other than these mishaps, the hotel was fine"
Reviewed on Jul 3, 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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