Historic Route 66 Vacations from $270
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The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $453, price is now $270 per person
$270
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
It was a great stay. The best part is breakfast till 10 am and noon checkout.
Reviewed on Dec 21, 2025
The Emily Hotel
Downtown Chicago
Price was $650, price is now $378 per person
$378
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Love staying at the Emily. Very helpful friendly Staff & ccool architecture. Also love the front Patio in Summer☀️
Reviewed on Dec 16, 2025
The Wildwood Hotel
Save 100% on your flight
Price was $688, price is now $403 per person
$403
per person
Feb 15 - Feb 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Another awesome uneventful evening
Just what I need!
Thanks, Wildwood Hotel
Reviewed on Dec 17, 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
$87 nightly
The price is $102 total per night from Dec 28 to Dec 29
$102 total
Dec 28 - Dec 29
Total with taxes and fees
8.6/10 Excellent! (3,316 reviews)
Great hotel
Reviewed on Dec 15, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Jan 5 to Jan 6
$105 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
8.8/10 Excellent! (3,522 reviews)
Clean room, few dust spots, warm and cozy stay
Reviewed on Dec 20, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $174 total per night from Dec 28 to Dec 29
$174 total
Dec 28 - Dec 29
Total with taxes and fees
8.4/10 Very Good! (2,153 reviews)
Staff was so amazing nice and helpfuk
Reviewed on Dec 20, 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.
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.
