Historic Route 66 Vacations from $661

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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
Hotel Riu Plaza Chicago
Fairmont Chicago at Millennium Park
Thompson Chicago, by Hyatt
Hilton Garden Inn Chicago Downtown South Loop
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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
$123 nightly
The price is $145 total per night from Mar 24 to Mar 25
$145 total
Mar 24 - Mar 25
Total with taxes and fees
8/10 Very Good! (9,999 reviews)
Stayed here because it was very convenient. Right across the street from the auditorium theater. St. Patrick’s Day parade, the next day, not far from the hotel. Very walkable. Terrific room with a great view, only downside it was chilly in the room, would love to have had more heat.

Reviewed on Mar 23, 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 Apr 6 to Apr 7
$183 total
Apr 6 - Apr 7
Total with taxes and fees
9.4/10 Exceptional! (3,603 reviews)
A beautiful hotel in the heart of downtown Chicago built in 2024. I have stayed at Riu Resorts outside the US and the Riu Plaza brought the same experience I received from the resorts. Amazing complimentary continental breakfast buffet, beautiful lobby, secured floor elevators, and clean workout ...

Reviewed on Mar 23, 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
$130 nightly
The price is $153 total per night from Apr 5 to Apr 6
$153 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (5,774 reviews)
The staff was super helpful and friendly. The room was clean and the bed was super comfortable! Perfect place to walk to lots of things.

Reviewed on Mar 22, 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

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English
Currency
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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.