Cheap Flights to Caldwell County from $89 (2026/2027)

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How Much Does it Cost To Fly To Caldwell County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jul 23 - Thu, Jul 23
ORD
O'Hare Intl.
MWA
Veterans Airport of Southern Illinois
$173 Roundtrip, found 4 hours ago
$173
Roundtrip
found 4 hours ago
Select Contour Airlines flight, departing Thu, Jul 23 from O'Hare Intl. to Veterans Airport of Southern Illinois, returning Thu, Jul 23, priced at $173 found 4 hours ago
Wed, Jul 29 - Tue, Aug 4
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$178 Roundtrip, found 4 hours ago
$178
Roundtrip
found 4 hours ago
Select Contour Airlines flight, departing Wed, Jul 29 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Tue, Aug 4, priced at $178 found 4 hours ago
Thu, Jul 23 - Mon, Jul 27
CLT
Charlotte-Douglas Intl.
OWB
Owensboro-Daviess County Regional
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Thu, Jul 23 from Charlotte-Douglas Intl. to Owensboro-Daviess County Regional, returning Mon, Jul 27, priced at $188 found 1 day ago
Sat, Aug 1 - Wed, Aug 5
ORD
O'Hare Intl.
PAH
Barkley Regional
$199 Roundtrip, found 7 hours ago
$199
Roundtrip
found 7 hours ago
Select United flight, departing Sat, Aug 1 from O'Hare Intl. to Barkley Regional, returning Wed, Aug 5, priced at $199 found 7 hours ago
Thu, Aug 13 - Sun, Aug 16
MCI
Kansas City Intl.
PAH
Barkley Regional
$274 Roundtrip, found 13 hours ago
$274
Roundtrip
found 13 hours ago
Select United flight, departing Thu, Aug 13 from Kansas City Intl. to Barkley Regional, returning Sun, Aug 16, priced at $274 found 13 hours ago
Fri, Aug 14 - Mon, Aug 17
MCI
Kansas City Intl.
EVV
Evansville Regional
$367 Roundtrip, found 2 days ago
$367
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Aug 14 from Kansas City Intl. to Evansville Regional, returning Mon, Aug 17, priced at $367 found 2 days ago
Sat, Aug 1 - Wed, Aug 5
JFK
John F. Kennedy Intl.
OWB
Owensboro-Daviess County Regional
$414 Roundtrip, found 1 day ago
$414
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Aug 1 from John F. Kennedy Intl. to Owensboro-Daviess County Regional, returning Wed, Aug 5, priced at $414 found 1 day ago
Sat, Aug 8 - Wed, Aug 12
ORD
O'Hare Intl.
EVV
Evansville Regional
$415 Roundtrip, found 2 days ago
$415
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Aug 8 from O'Hare Intl. to Evansville Regional, returning Wed, Aug 12, priced at $415 found 2 days ago
OriginDestinationTravel DatesFlights From*
ORDMarionJuly 23 to July 23$173
ORDOwensboroJuly 29 to August 4$178
ORDWest PaducahAugust 1 to August 5$199
DFWWest PaducahOctober 2 to October 16$294
SEAWest PaducahSeptember 5 to September 12$346
IADEvansvilleJuly 29 to August 1$392
DFWEvansvilleOctober 15 to October 20$405
DFWMarionAugust 27 to September 1$409
ORDEvansvilleAugust 8 to August 12$415
DFWOwensboroSeptember 25 to September 27$476
SANEvansvilleSeptember 24 to September 27$519
SEAEvansvilleAugust 18 to August 23$539
SANOwensboroJuly 23 to July 27$681
SEAMarionAugust 13 to August 19$712
COSWest PaducahJuly 31 to August 2$796
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDOwensboroJuly 12 to July 26$289
ORDMarionJuly 12 to July 12$343
COSEvansvilleJuly 11 to July 18$476
ORDWest PaducahJuly 12 to July 18$577
DFWEvansvilleJuly 10 to July 11$641
*Prices include taxes and fees

Travelers ❤️ These Caldwell County 🏨

Kentucky Dam Village State Resort Park

Kentucky Dam Village State Resort Park

3 out of 5
166 upper village Dr Gilbertsville KY
Book a stay at this beach hotel in Gilbertsville. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Patti's Settlement 1880's and Kentucky Lake are located nearby.
9/10 Wonderful! (1,155 reviews)
"It was a clean and decent room! Just wished the ac could’ve got the room cooler and the bugs could’ve stayed out. Other than that will be back to stay again!"

Reviewed on Jul 8, 2026

Opens in a new windowKentucky Dam Village State Resort Park
Days Inn by Wyndham Madisonville

Days Inn by Wyndham Madisonville

2 out of 5
1900 Lantaff Blvd Madisonville KY
Stay at this hotel in Madisonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Mahr Park and Kentucky Sports Factory are located nearby.
7/10 Good! (940 reviews)
"Propiedad oscura , húmeda y todo antiguo por el precio que tiene no lo recomiendo nunca"

Reviewed on Jul 5, 2026

Opens in a new windowDays Inn by Wyndham Madisonville
Pennyrile Forest State Resort Park

Pennyrile Forest State Resort Park

3.5 out of 5
20781 Pennyrile Lodge Road Dawson Springs KY
Book a stay at this golf hotel in Dawson Springs. Enjoy free breakfast, free WiFi, and free parking. Popular attraction Pennyrile Forest State Resort Park is located nearby.
9/10 Wonderful! (273 reviews)
"Clean room"

Reviewed on Jul 4, 2026

Opens in a new windowPennyrile Forest State Resort Park
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Hotel Barkley

Hotel Barkley

2 out of 5
139 Days Inn Drive Kuttawa KY
Stay at this motel in Kuttawa. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Kuttawa Harbor Marina and Vista Ridge Park are located nearby.
9/10 Wonderful! (102 reviews)
"Def not as the reviews led Clean but aged Safe area but nothing around limited restaurant choices"

Reviewed on Jul 8, 2026

Opens in a new windowHotel Barkley
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.

Frequently asked questions

How much is the cheapest flight to Caldwell County?
Your next trip doesn't have to break the bank. Within the last seven days, the cheapest return flight to Caldwell County cost $173. Find a cheap seat and spend the money you save on cool experiences. This price was available on Travelocity for flights to Caldwell County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Caldwell County?
Book your seat with one of the 15 airlines that fly to Caldwell County. If you're heading to Princeton, let United Airlines whisk you away to this dynamic city to enjoy its iconic attractions. This reputable carrier offers 60 flights there per month.
What is the cheapest month to fly to Caldwell County?
If you're thinking of booking a trip to Caldwell County, July is the cheapest month to fly there. This is according to Travelocity's direct return flight demand from January to December last year. Choose your ideal travel dates and reserve your seat today.
How can I check my flight status to Caldwell County?
"Trips" has you covered when it comes to the details of your flight to Caldwell County. Travelocity's customer portal lets you organize everything in the one place, from looking up your flight status to updating or canceling your booking. Click on Trips at the top right of the Travelocity homepage and then sign in to your account or create a new one. You can also download the Travelocity app and access your info while you're out and about. Whether you have the family flying with you or you're a lone adventurer, all your bookings are right there in your grasp.
How do I find the best deals on flights to Caldwell County?
Being flexible with your travel dates is one way to pick up a bargain. Travelocity makes it a piece of cake to find your perfect fare through the "Flexible dates" feature. First, search for your Caldwell County flight, then compare the cheapest prices for surrounding dates by hitting the Flexible dates dropdown box above. Booking well in advance and flying outside of peak periods will also help you save. In the last seven days, the cheapest price for a roundtrip flight to Caldwell County was $173 on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Caldwell County with Travelocity?
Search for cheap flights to Caldwell County with Travelocity and begin arranging your next escape. With 24/7 personal assistance along every step of your trip and a Price Match Guarantee, we take the stress out of securing cheap family flights, hotels, rental cars and more. Lock in a fantastic deal today and prepare yourself for a wonderful adventure.
What are the most popular flight routes to Caldwell County?
To help you choose your flights to Caldwell County, check out our list of some of the preferred routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Nashville Intl. Airport (BNA) - 2,491 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Nashville Intl. Airport (BNA) - 1,932 flights a month.
  • New York, NY (LGA-LaGuardia) to Nashville Intl. Airport (BNA) - 1,911 flights a month.

How much is a flight to Caldwell County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Caldwell County were between $173 and $796. Whenever you're ready to jet off, Travelocity will help you find a fare to fit your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Caldwell County?
Where you leave from will usually dictate how many hours your direct flight to Caldwell County will take. Here are some of the more popular routes to Caldwell County and their average flight times:

  • Chicago, IL (ORD-O'Hare Intl.) to Nashville Intl. Airport (BNA) - 1 hour and 34 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Nashville Intl. Airport (BNA) - 1 hour and 5 minutes
  • New York, NY (LGA-LaGuardia) to Nashville Intl. Airport (BNA) - 2 hours and 26 minutes

What can I expect on a flight to Caldwell County?
Factors such as which airline you're flying with and where your plane takes off from will largely determine what inclusions and services you can expect. You'll likely find a range of flights to Caldwell County, from cheap flights for family vacations to premium airfares. Hot meals, entertainment and games for the kids are just a small taste what most airlines offer on long-haul flights.