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.

Sat, Sep 5 - Sun, Sep 6
ORD
O'Hare Intl.
MWA
Veterans Airport of Southern Illinois
$178 Roundtrip, found 3 days ago
$178
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Sat, Sep 5 from O'Hare Intl. to Veterans Airport of Southern Illinois, returning Sun, Sep 6, priced at $178 found 3 days ago
Tue, Sep 22 - Tue, Sep 29
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Tue, Sep 22 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Tue, Sep 29, priced at $178 found 1 day ago
Thu, Sep 10 - Tue, Sep 15
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$181 Roundtrip, found 3 hours ago
$181
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Thu, Sep 10 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Tue, Sep 15, priced at $181 found 3 hours ago
Thu, Oct 1 - Mon, Oct 5
ORD
O'Hare Intl.
PAH
Barkley Regional
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Oct 1 from O'Hare Intl. to Barkley Regional, returning Mon, Oct 5, priced at $197 found 2 hours ago
Sat, Oct 24 - Sat, Oct 31
ORD
O'Hare Intl.
MWA
Veterans Airport of Southern Illinois
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 24 from O'Hare Intl. to Veterans Airport of Southern Illinois, returning Sat, Oct 31, priced at $205 found 1 day ago
Thu, Sep 17 - Sat, Sep 19
DSM
Des Moines Intl.
PAH
Barkley Regional
$288 Roundtrip, found 21 hours ago
$288
Roundtrip
found 21 hours ago
Select United flight, departing Thu, Sep 17 from Des Moines Intl. to Barkley Regional, returning Sat, Sep 19, priced at $288 found 21 hours ago
Thu, Sep 3 - Thu, Sep 10
DTW
Detroit Metropolitan Wayne County
PAH
Barkley Regional
$338 Roundtrip, found 18 hours ago
$338
Roundtrip
found 18 hours ago
Select United flight, departing Thu, Sep 3 from Detroit Metropolitan Wayne County to Barkley Regional, returning Thu, Sep 10, priced at $338 found 18 hours ago
Fri, Oct 30 - Sun, Nov 1
DTW
Detroit Metropolitan Wayne County
EVV
Evansville Regional
$377 Roundtrip, found 18 hours ago
$377
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Fri, Oct 30 from Detroit Metropolitan Wayne County to Evansville Regional, returning Sun, Nov 1, priced at $377 found 18 hours ago
OriginDestinationTravel DatesFlights From*
ORDOwensboroSeptember 22 to September 29$178
CLTOwensboroSeptember 17 to September 23$188
ORDWest PaducahOctober 1 to October 5$197
ORDMarionOctober 24 to October 31$205
DFWWest PaducahSeptember 17 to September 20$308
TPAEvansvilleOctober 28 to October 31$309
TPAWest PaducahOctober 23 to October 25$319
CLTMarionSeptember 19 to September 21$378
COSEvansvilleSeptember 10 to September 12$419
DFWOwensboroSeptember 15 to September 20$462
ORDEvansvilleSeptember 12 to September 13$491
CLTEvansvilleSeptember 12 to September 14$509
CLTWest PaducahNovember 19 to November 21$585
CLDMarionSeptember 25 to October 8$592
SEAOwensboroSeptember 23 to September 25$639
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CLTOwensboroAugust 28 to September 7$251
ORDMarionAugust 29 to August 30$353
ORDOwensboroAugust 29 to August 31$373
COSEvansvilleAugust 28 to August 30$587
DFWEvansvilleAugust 28 to August 29$628
*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 Kentucky Lake and Kentucky Dam Marina are located nearby.
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! (966 reviews)
"Had to change room 3 times. 1st time musky and stinky, 2nd room black mold 3rd time clean and fresh smelling. 2nd night of stay people couple rooms came in at 1:30 and party until 4:00 unacceptable. Last night of stay quiet and peaceful"

Reviewed on Aug 24, 2026

Opens in a new windowDays Inn by Wyndham Madisonville
Baymont by Wyndham Madisonville

Baymont by Wyndham Madisonville

2.5 out of 5
1891 Lantaff Blvd Madisonville KY
Stay at this hotel in Madisonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Mahr Park and Kentucky Sports Factory are located nearby.
8/10 Very Good! (373 reviews)
"You get what you pay for and this place was cheap. Not bad but not great."

Reviewed on Aug 21, 2026

Opens in a new windowBaymont by Wyndham Madisonville
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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.
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 $178. 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, September 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 $178 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 $178 and $639. 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.