Historic Route 66 Vacations from $379
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.
The Wildwood Hotel
Save 100% on your flight
Price was $683, price is now $379 per person
$379
per person
May 8 - May 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,620 reviews)
Clean - hot tub was really small - pool area was very loud - there were people down the hall that were loud and we heard doors opening and closing most of the night
Reviewed on Mar 13, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,834, price is now $1,094 per person
$1,094
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Comfy beds, great staff, great shower, great breakfast
Reviewed on Mar 13, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,083, price is now $665 per person
$665
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,076 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026
Don't see what you're looking for?
See all available trips from Columbus to Historic Route 66
View all trips
Historic Route 66 Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $118 total per night from Apr 1 to Apr 2
$118 total
Apr 1 - Apr 2
Total with taxes and fees
8/10 Very Good! (9,922 reviews)
The location is amazing, right on Michigan Avenue, across the street from the park, a few blocks south of the river. The staff was friendly and efficient when I checked in, asked a few questions, and checked out. The room was great... nicer than I imagined. I would have liked daily room service. ...
Reviewed on Mar 14, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $183 total per night from Mar 22 to Mar 23
$183 total
Mar 22 - Mar 23
Total with taxes and fees
9.4/10 Exceptional! (3,527 reviews)
Clean, central and amazing breakfast
Reviewed on Mar 13, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $151 total per night from Mar 15 to Mar 16
$151 total
Mar 15 - Mar 16
Total with taxes and fees
8.6/10 Excellent! (5,736 reviews)
Great location. Good amenities. Nice breakfast. Comfy beds. Quiet.
Reviewed on Mar 12, 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.
