Historic Route 66 Vacations from $402
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 $629, price is now $402 per person
$402
per person
May 31 - Jun 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,620 reviews)
the hotel is very comfortable and the staff was very helpful.
Reviewed on Mar 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,521, price is now $844 per person
$844
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
We loved the breakfast and how convenient the hotel is from the Magnificent Mile and the river walk.
Reviewed on Mar 23, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,013, price is now $661 per person
$661
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Staff were great in dealing with many of our needs
Reviewed on Mar 22, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Save 100% on your flight
Price was $2,488, price is now $1,654 per person
$1,654
per person
May 29 - Jun 1
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,332 reviews)
Clean rooms and friendly staff
Reviewed on Mar 22, 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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $145 total per night from Mar 24 to Mar 25
$145 total
Mar 24 - Mar 25
Total with taxes and fees
8/10 Very Good! (9,997 reviews)
renovate room barhroom
Reviewed on Mar 22, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$162 nightly
The price is $190 total per night from Mar 29 to Mar 30
$190 total
Mar 29 - Mar 30
Total with taxes and fees
9.4/10 Exceptional! (3,600 reviews)
We loved the breakfast and how convenient the hotel is from the Magnificent Mile and the river walk.
Reviewed on Mar 23, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $153 total per night from Apr 5 to Apr 6
$153 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (5,773 reviews)
The staff was super helpful and friendly. The room was clean and the bed was super comfortable! Perfect place to walk to lots of things.
Reviewed on Mar 22, 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.
