Cheap Flights to Caldwell County from $53 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

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, Aug 22 - Sat, Aug 29
MCO
Orlando Intl.
EVV
Evansville Regional
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Aug 22 from Orlando Intl. to Evansville Regional, returning Sat, Aug 29, priced at $102 found 1 day ago
Sat, Aug 22 - Sat, Aug 29
MCO
Orlando Intl.
EVV
Evansville Regional
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Aug 22 from Orlando Intl. to Evansville Regional, returning Sat, Aug 29, priced at $107 found 1 day ago
Sat, Aug 22 - Sat, Aug 29
MCO
Orlando Intl.
EVV
Evansville Regional
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Aug 22 from Orlando Intl. to Evansville Regional, returning Sat, Aug 29, priced at $112 found 1 day ago
Fri, Sep 4 - Fri, Sep 4
ORD
O'Hare Intl.
MWA
Veterans Airport of Southern Illinois
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Fri, Sep 4 from O'Hare Intl. to Veterans Airport of Southern Illinois, returning Fri, Sep 4, priced at $177 found 2 hours ago
Fri, Sep 18 - Sun, Sep 20
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$178 Roundtrip, found 3 hours ago
$178
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Fri, Sep 18 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Sun, Sep 20, priced at $178 found 3 hours ago
Sat, Aug 1 - Wed, Aug 5
ORD
O'Hare Intl.
PAH
Barkley Regional
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Aug 1 from O'Hare Intl. to Barkley Regional, returning Wed, Aug 5, priced at $199 found 1 hour ago
Fri, Oct 2 - Fri, Oct 16
DFW
Dallas-Fort Worth Intl.
PAH
Barkley Regional
$294 Roundtrip, found 2 days ago
$294
Roundtrip
found 2 days ago
Select United flight, departing Fri, Oct 2 from Dallas-Fort Worth Intl. to Barkley Regional, returning Fri, Oct 16, priced at $294 found 2 days ago
Wed, Aug 26 - Sun, Aug 30
MCO
Orlando Intl.
PAH
Barkley Regional
$301 Roundtrip, found 2 hours ago
$301
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Aug 26 from Orlando Intl. to Barkley Regional, returning Sun, Aug 30, priced at $301 found 2 hours ago
Wed, Nov 18 - Wed, Dec 2
MCO
Orlando Intl.
EVV
Evansville Regional
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Nov 18 from Orlando Intl. to Evansville Regional, returning Wed, Dec 2, priced at $314 found 1 day ago
Wed, Jan 13 - Wed, Jan 20
MCO
Orlando Intl.
EVV
Evansville Regional
$391 Roundtrip, found 1 day ago
$391
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jan 13 from Orlando Intl. to Evansville Regional, returning Wed, Jan 20, priced at $391 found 1 day ago
Thu, Oct 15 - Tue, Oct 20
DFW
Dallas-Fort Worth Intl.
EVV
Evansville Regional
$405 Roundtrip, found 6 hours ago
$405
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Oct 15 from Dallas-Fort Worth Intl. to Evansville Regional, returning Tue, Oct 20, priced at $405 found 6 hours ago
OriginDestinationTravel DatesFlights From*
ORDMarionAugust 21 to August 21$177
ORDOwensboroJuly 29 to August 12$178
ORDWest PaducahAugust 1 to August 5$199
ATLEvansvilleAugust 2 to August 10$286
DFWWest PaducahOctober 2 to October 16$294
TPAWest PaducahSeptember 9 to September 13$294
SEAWest PaducahSeptember 5 to September 12$346
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
SEAMarionAugust 13 to August 19$712
COSWest PaducahJuly 31 to August 2$796
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CLTOwensboroJuly 10 to July 12$315
ORDMarionJuly 12 to July 12$343
ORDOwensboroJuly 12 to July 15$376
COSEvansvilleJuly 11 to July 18$476
ORDWest PaducahJuly 12 to July 18$577
DFWEvansvilleJuly 10 to July 11$641
*Prices include taxes and fees

Best Caldwell County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Hopkinsville
3.0-star property

La Quinta Inn & Suites by Wyndham Hopkinsville

Sep 24 - Sep 26

2 night stay

San Diego (SAN) to Paducah (PAH)

Southwest Airlines • Roundtrip • Coach
Price was $388, price is now $365 per person
$365
per person
found 1 day ago
Early American Motel
2.0-star property

Early American Motel

Sep 24 - Sep 26

2 night stay

San Diego (SAN) to Paducah (PAH)

Southwest Airlines • Roundtrip • Coach
Price was $408, price is now $370 per person
$370
per person
found 1 day ago
Best Western University Inn
2.5-star property

Best Western University Inn

Sep 24 - Sep 26

2 night stay

San Diego (SAN) to Paducah (PAH)

Southwest Airlines • Roundtrip • Coach
Price was $434, price is now $398 per person
$398
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from San Diego to Caldwell County
View all trips

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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 $102. 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 20 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, August 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 $102 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 $102 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.