Historic Route 66 Vacations from $390

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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
Still Waters Resort
LondonHouse Chicago, Curio Collection by Hilton
Thompson Chicago, by Hyatt
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Historic Route 66 Hotel Deals

Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street Chicago IL
$93 nightly
The price is $109 total per night from Apr 9 to Apr 10
$109 total
Apr 9 - Apr 10
Total with taxes and fees
8.6/10 Excellent! (2,054 reviews)
everything was nice

Reviewed on Apr 8, 2026

Central Loop Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $137 total per night from Apr 26 to Apr 27
$137 total
Apr 26 - Apr 27
Total with taxes and fees
8/10 Very Good! (10,062 reviews)
Great location but very old and run down..needs updates

Reviewed on Apr 7, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with taxes and fees
9/10 Wonderful! (4,075 reviews)
Staff was very friendly and helpful! Food in restaurant was very good. Very clean!!

Reviewed on Apr 8, 2026

Hilton Chicago/Magnificent Mile Suites
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.