Historic Route 66 Vacations from $786

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
The Wildwood Hotel
Hotel Riu Plaza Chicago
The Wade
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Historic Route 66 Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
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! (9,942 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

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
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! (3,508 reviews)
Clean, amazing terrace, bad and breakfast.

Reviewed on Mar 10, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
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

Embassy Suites by Hilton Chicago Downtown River North
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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