Historic Route 66 Vacations from $203
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Prospect Heights by IHG
Save 100% on your flight
Price was $344, price is now $203 per person
$203
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (851 reviews)
Clan quiet room. Comfortable bed. Great staff. Need to upgrade the fitness center
Reviewed on Nov 11, 2025
Westgate Branson Woods Resort and Cabins
Shepherd of the Hills
Save 100% on your flight
Price was $1,160, price is now $659 per person
$659
per person
Jan 2 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (SGF)
7.8/10 Good! (1,029 reviews)
Its always a great time staying there
Reviewed on Nov 11, 2025
Sand Hill On The Lake
Price was $500, price is now $284 per person
$284
per person
Dec 31 - Jan 3
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (77 reviews)
The view on the lake is beautiful and the fireplace made it so cozy during our fall visitl
Reviewed on Nov 10, 2025
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Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $107 total per night from Nov 23 to Nov 24
$107 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (3,297 reviews)
I had no issues
Reviewed on Nov 12, 2025
Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $107 total per night from Nov 23 to Nov 24
$107 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,884 reviews)
Great
Reviewed on Nov 8, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $112 total per night from Nov 25 to Nov 26
$112 total
Nov 25 - Nov 26
Total with taxes and fees
8.4/10 Very Good! (5,235 reviews)
Clean room; kind and courteous staff; excellent breakfast and happy hour included
Reviewed on Nov 10, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.