Historic Route 66 Vacations from $382
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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 $702, price is now $382 per person
$382
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,620 reviews)
First time in the St. louis area & staying at this hotel. The property was in a great little location that wasn’t overly far from St. louis. The staff were lovely and very kind. Our room actually go upgraded for free as well as a free beverage due to my expedia status (i’ve done lots of traveling but have never had this before). The breakfast was decent, there was lots of options for everyone. We didn’t have the opportunity to use the pool or hot tub but there was always people in the area and looked very clean. Overall very impressed and would come back!
Reviewed on Mar 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,156, price is now $678 per person
$678
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
The room was very nice and the free breakfast was wonderful!
Reviewed on Mar 17, 2026
Level Chicago – Old Town
Downtown Chicago
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Price was $1,330, price is now $828 per person
$828
per person
May 26 - May 30
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Interesting property in that it is a high rise building of furnished suites with certain floors available as a “hotel”. Coffee shop, gym and lounge are all nice as are the suites. Just know this is not a service oriented hotel experience. No doorman, uniformed person at desk, room or maid service etc.
Reviewed on Mar 14, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,136, price is now $721 per person
$721
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Great location and nicely maintained rooms
Reviewed on Mar 17, 2026
Rosewood Inn of the Anasazi
Downtown Santa Fe
Save 100% on your flight
Price was $2,938, price is now $1,995 per person
$1,995
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Albuquerque (ABQ)
9.6/10 Exceptional! (881 reviews)
Rooms were very nice. Staff was very friendly and accommodating. Would definitely stay here again.
Reviewed on Feb 27, 2026
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View all tripsHistoric Route 66 Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Mar 19 to Mar 20
$140 total
Mar 19 - Mar 20
Total with taxes and fees
8/10 Very Good! (9,951 reviews)
As a solo traveller, the queen room with a private bathroom was perfectly priced and a real treat to stay in! I don't believe I encountered any ghosts, but the plumbing was a bit scary. Veeeery low water-pressure in the shower, and the toilet should really have a sign to hold down the flush lever ...
Reviewed on Mar 17, 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! (3,547 reviews)
The room was very nice and the free breakfast was wonderful!
Reviewed on Mar 17, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$130 nightly
The price is $153 total per night from Mar 23 to Mar 24
$153 total
Mar 23 - Mar 24
Total with taxes and fees
8.6/10 Excellent! (5,752 reviews)
Good
Reviewed on Mar 16, 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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