Historic Route 66 Vacations from $434
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Oak Lawn
Save 100% on your flight
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,002 reviews)
The staff at both check in and check out were so pleasant to deal with. They made us feel very welcome.
Reviewed on Aug 11, 2025
The Royal Sonesta Chicago River North
Downtown Chicago
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Rooms were very clean and spacious! The inside of the property was very clean, staff were extremely helpful and caring! The area around/ outside didn't feel the safest, they did have a security guard outside at all times. I would not stay in this location with our children again because of safety concerns.
Reviewed on Aug 10, 2025
The Wade
Downtown Chicago
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,156 reviews)
This hotel did not have coffee machines in the room! However you could take the 25 floor ride to the lobby and get free coffee. This hotel did not offer complimentary Wi-Fi in the room but you could take the 25 floor ride to the lobby and get free Wi-Fi. Don’t park at this hotel with a truck because it will cost you $86 per day!!
Reviewed on Aug 10, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
The location was good. Staff was friendly. It was clean. But it was hard to enjoy time in the room because of the TV. They had horrible cable with nothing on, and it wasn’t a smart tv so we couldn’t log into any of our streaming services or even stream from our phones to the tv. We had to go out and buy a firestick.
Reviewed on Aug 10, 2025
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View all tripsHistoric Route 66 Hotel Deals
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundable
$122 nightly
The price is $144 total per night from Sep 4 to Sep 5
$144 total
Sep 4 - Sep 5
Total includes taxes and fees
8.6/10 Excellent! (3,345 reviews)
"Nice that it's near the Food Hall and a few minutes walk from Grant Park."
Reviewed on Aug 8, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,943 reviews)
"The hotel room was quiet and clean, only a little old and something outdated but still functional (tv). The area is great to visit a lot of the Chicago attractions and staff was helpful. Would recommend!"
Reviewed on Aug 11, 2025
The Aquarius Casino Resort, BW Premier Collection
1900 S Casino Dr, Laughlin, NV
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $70 total per night from Aug 12 to Aug 13
$70 total
Aug 12 - Aug 13
Total includes taxes and fees
8/10 Very Good! (6,761 reviews)
"I hope PickUp Stix gets replaced by something even better! We need a good, lighter alternative"
Reviewed on Aug 10, 2025
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.
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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.