Historic Route 66 Vacations from $541
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Still Waters Resort
Save 100% on your flight
Price was $838, price is now $541 per person
$541
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (SGF)
8.8/10 Excellent! (4,555 reviews)
Property is well maintained in the view is spectacular
Reviewed on Mar 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,575, price is now $848 per person
$848
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Staff was really nice and polite, Portuguese and Spanish speakers which was a must and breakfast buffet was amazing, highly recommended!
Reviewed on Mar 15, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,367, price is now $837 per person
$837
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,109, price is now $688 per person
$688
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on Mar 4, 2026
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,202, price is now $775 per person
$775
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street
Reviewed on Mar 12, 2026
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Historic Route 66 Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $121 total per night from Apr 1 to Apr 2
$121 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,934 reviews)
It was everything we needed it to be but the bed felt like laying on soft carpet. Why is it so firm that it didn’t even mold to my body?
Reviewed on Mar 15, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $183 total per night from Mar 22 to Mar 23
$183 total
Mar 22 - Mar 23
Total with taxes and fees
9.4/10 Exceptional! (3,536 reviews)
Staff was really nice and polite, Portuguese and Spanish speakers which was a must and breakfast buffet was amazing, highly recommended!
Reviewed on Mar 15, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $144 total per night from Mar 22 to Mar 23
$144 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (5,743 reviews)
Yes great
Reviewed on Mar 15, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
