
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
Save 100% on your flight
Price was $372, price is now $228 per person
$228
per person
May 20 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,002 reviews)
Hotel was nice, good food choices and parking was great, easily accessible. I expected a bit more for such a well known hotel.
Reviewed on Apr 13, 2026

The Wildwood Hotel
Save 100% on your flight
Price was $754, price is now $392 per person
$392
per person
Jun 24 - Jun 27
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,624 reviews)
Poor quality breakfast buffet, unsecured parking, worn furnishings, in need of a redo. Overpriced for conditions.
Reviewed on Apr 17, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,048, price is now $586 per person
$586
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Staff was a little grumpy and our room wasn’t ready even though it was well past check in time. However once we got in the property was excellent—very comfortable beds. And the breakfast was outstanding.
Reviewed on Apr 18, 2026

Harwelden Mansion
Maple Ridge
Save 100% on your flight
Price was $1,596, price is now $957 per person
$957
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Tulsa (TUL)
10/10 Exceptional! (34 reviews)
Staff was great, rooms were very clean.
Reviewed on Mar 26, 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $904, price is now $559 per person
$559
per person
Jun 26 - Jun 29
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
It’s a bit loud on the weekend. There is no daily housekeeping but great space and great location.
Reviewed on Apr 17, 2026
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Central Loop Hotel
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

Hilton Chicago/Magnificent Mile Suites
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

Embassy Suites by Hilton Chicago Downtown River North
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
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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