Historic Route 66 Vacations from $334

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza St. Louis Airport by IHG
Hotel Riu Plaza Chicago
Level Chicago – Old Town
The Wildwood Hotel
Still Waters Resort
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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
$103 nightly
The price is $121 total per night from Apr 1 to Apr 2
$121 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,963 reviews)
Very tired hotel in need of renovation

Reviewed on Mar 19, 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! (3,566 reviews)
Clean room, courteous staff,

Reviewed on Mar 19, 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 Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (5,743 reviews)
Good room lower floor was a little close to the street and a little loud but it’s Chicago so to be expected. Breakfast was good and the room was clean.

Reviewed on Mar 18, 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.