Historic Route 66 Vacations from $460
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Historic Route 66 vacation packages
Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
Save 100% on your flight
Price was $686, price is now $460 per person
$460
per person
Jun 23 - Jun 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8/10 Very Good! (504 reviews)
Waited 15min to check in. Received an apology along with an explanation of having to do three jobs at once. Shower ceiling had peeling paint with mildew/mold stains. Vanity would not drain. Was relocated to another RM.
Reviewed on Apr 1, 2026
The Wildwood Hotel
Save 100% on your flight
Price was $1,133, price is now $629 per person
$629
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,620 reviews)
The breakfaat was average, thou fresh. There was enough street parking nearby, safe.
Reviewed on Mar 30, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $773, price is now $472 per person
$472
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was perfect. The staff are really friendly and helpful. Love it!!! Definitely I'll come back
Reviewed on Apr 1, 2026
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Save 100% on your flight
Price was $786, price is now $548 per person
$548
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.4/10 Very Good! (999 reviews)
Beautiful rooms and casino i cant wait to return
Reviewed on Mar 2, 2026
Don't see what you're looking for?
See all available trips from Columbus to Historic Route 66
View all tripsHistoric Route 66 Hotel Deals
Central Loop Hotel
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Apr 6 to Apr 7
$109 total
Apr 6 - Apr 7
Total with taxes and fees
8.6/10 Excellent! (2,052 reviews)
I went down for breakfast at 7.30 am when I returned an hour later someone had been in my room my reservation strongly states that I'm leaving checkout is at 12:00 why was a hair dryer in my chair that I don't use and the one for the room is in the closet. I didn't appreciate it at all.
Reviewed on Apr 1, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from Apr 5 to Apr 6
$125 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (10,036 reviews)
Clean
Reviewed on Apr 1, 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 8 to Apr 9
$140 total
Apr 8 - Apr 9
Total with taxes and fees
9/10 Wonderful! (4,029 reviews)
Overall a great place. My only issue was that they charged us for 3 nights of valet @82.00, but we only had a car there for one night.
Reviewed on Apr 1, 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 |
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
