Historic Route 66 Vacations from $228

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The Latest Historic Route 66 vacation packages

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
The Wildwood Hotel
Hotel Riu Plaza Chicago
Harwelden Mansion
Level Chicago – Old Town
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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
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Apr 19 to Apr 20
$136 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (2,080 reviews)
Carpet in the room was smelly and paper thin walls, we could hear all the noise from the hallway ALL NIGHT! The people at the front desk were not friendly, telling us to come back at 11 am for the check in to later tell us to come at 1 to then tell us that the room will be ready at 3. Lots of guests ...

Reviewed on Apr 18, 2026

Central Loop 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! (4,149 reviews)
The room was overheated and I could not turn the air system off. I put it on 60 and whether it was AC or heat (my options), the room was always at least 75 but I was able to open a window beside my bed which helped.

Reviewed on Apr 18, 2026

Hilton Chicago/Magnificent Mile Suites
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
$139 nightly
The price is $163 total per night from Apr 26 to Apr 27
$163 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (5,856 reviews)
Clean and easy check in.

Reviewed on Apr 17, 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
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.