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
Hotel Riu Plaza Chicago
Level Chicago – Old Town
Fairmont Chicago at Millennium Park
Rosewood Inn of the Anasazi
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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
$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

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
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

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
$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

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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