Historic Route 66 Vacations from $355
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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 $1,085, price is now $679 per person
$679
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everyone that we encountered at the hotel was so helpful and so nice.
Reviewed on Mar 11, 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
$101 nightly
The price is $118 total per night from Apr 1 to Apr 2
$118 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,943 reviews)
I like this hotel. It’s simple, clean, no frills and gets the job done. Hallways carpets are a little worse for wear but the room serves the purpose - you get what you reserve! - and you’re close to everything. It’s a “go to” for me.
Reviewed on Mar 10, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
$162 nightly
The price is $190 total per night from Mar 24 to Mar 25
$190 total
Mar 24 - Mar 25
Total with taxes and fees
9.4/10 Exceptional! (3,511 reviews)
Everyone that we encountered at the hotel was so helpful and so nice.
Reviewed on Mar 11, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$122 nightly
The price is $143 total per night from Mar 22 to Mar 23
$143 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (5,725 reviews)
Great location. Room was very hot. U can't switch heat to AC in the rooms. U just have to deal with what the hotel has it on. Also they would only give us one little fan to cool off. Not 2 which I'm sure they had plenty of. Other then that no complaints. They give a free happy hour with 2 free drinks ...
Reviewed on Mar 11, 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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