Historic Route 66 Vacations from $327
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton
Grand Center
Save 100% on your flight
Price was $500, price is now $327 per person
$327
per person
Oct 29 - Nov 2
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.8/10 Excellent! (1,005 reviews)
The rooms are so beautiful and colorful! The rooftop bar was really fun and the DJ had the right groove going with the breeze and the view 10’s across the board. I will be back real soon!!
Reviewed on Sep 24, 2025
The Wildwood Hotel
Price was $734, price is now $350 per person
$350
per person
Oct 29 - Nov 2
found 3 hours ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,581 reviews)
It was great being next to a police station! and the parking attached to the building, sweet! Felt safe and had no problems walking around the area.
Only negative was attempting to go walk on the treadmill at 5:30 when the fitness center doesn't open until 7. However that was not a big issue.
Reviewed on Sep 27, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,310, price is now $738 per person
$738
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September.
Rooms were clean modern and had loads of desk space but no dressers or nightstands.
Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily.
We would stay there again.
Reviewed on Sep 26, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $763, price is now $443 per person
$443
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay. Clean and quiet and conveniently located to all types of eating, shopping, and river walk.
Great breakfast buffet to start the day and fantastic rooftop bar for the evening!
Reviewed on Sep 28, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $891, price is now $572 per person
$572
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe
Reviewed on Sep 27, 2025
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
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundable
$168 nightly
The price is $197 total per night from Oct 5 to Oct 6
$197 total
Oct 5 - Oct 6
Total with taxes and fees
8.6/10 Excellent! (3,370 reviews)
"Decent property overall."
Reviewed on Sep 25, 2025
Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $197 total per night from Oct 5 to Oct 6
$197 total
Oct 5 - Oct 6
Total with taxes and fees
8.4/10 Very Good! (1,867 reviews)
"Friendly and helpful staff. Perfect location!!"
Reviewed on Sep 23, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Oct 26 to Oct 27
$179 total
Oct 26 - Oct 27
Total with taxes and fees
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."
Reviewed on Sep 25, 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.
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.
