Historic Route 66 Vacations from $231

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Louis, Autograph Collection
Hotel Riu Plaza Chicago
JW Marriott Chicago
The Wildwood Hotel
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
$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! (9,924 reviews)
Staff is very polite and friendly! Grant gardens and bus stops are very convenient. Beautiful views. Historical building and safe feeling.

Reviewed on Mar 7, 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! (3,476 reviews)
Outstanding hotel with a great location

Reviewed on Mar 7, 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
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $144 total per night from Mar 19 to Mar 20
$144 total
Mar 19 - Mar 20
Total with taxes and fees
8.6/10 Excellent! (5,724 reviews)
No airport shuttle. Great breakfast and afternoon snacks. Hector is extremely nice. No one answers the phone, but will respond to a text message most of the time. A group of teenagers ran the hallway with minimal supervision.

Reviewed on Mar 8, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.