Historic Route 66 Vacations from $309
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $488, price is now $309 per person
$309
per person
May 8 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!
Reviewed on Mar 19, 2026
The Wildwood Hotel
Save 100% on your flight
Price was $1,112, price is now $695 per person
$695
per person
May 21 - May 26
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to St. Louis (STL)
9.2/10 Wonderful! (1,620 reviews)
Very nice, clean and there is a pool, a small gym and access to good things in the area
Reviewed on Mar 18, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $1,260, price is now $812 per person
$812
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Nice room, fun rooftop bar, late to check in, room wasn’t ready but it was St Patty’s day so lots of revelers.
Reviewed on Mar 18, 2026
Crowne Plaza St. Louis Airport by IHG
Save 100% on your flight
Price was $505, price is now $334 per person
$334
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8/10 Very Good! (1,007 reviews)
Centrally located, great park and fly, breakfast is great. The only thing I do not like is for police officers to park outside and go to eat breakfast. It appears that there is trouble at the hotel.
Reviewed on Mar 9, 2026
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Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $141 total per night from Mar 22 to Mar 23
$141 total
Mar 22 - Mar 23
Total with taxes and fees
8/10 Very Good! (9,974 reviews)
I spent 2 nights and everything was great. I'll be back!
Reviewed on Mar 18, 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 24 to Mar 25
$183 total
Mar 24 - Mar 25
Total with taxes and fees
9.4/10 Exceptional! (3,565 reviews)
It was a wonderful visit with not one complaint about the amenities, cleanliness or staff!
Reviewed on Mar 19, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (5,743 reviews)
Good room lower floor was a little close to the street and a little loud but it’s Chicago so to be expected. Breakfast was good and the room was clean.
Reviewed on Mar 18, 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.
