
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.
ORD
O'Hare Intl.
MWA
Veterans Airport of Southern Illinois
$173 Roundtrip, found 4 hours ago
$173
Roundtrip
found 4 hours ago
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$178 Roundtrip, found 4 hours ago
$178
Roundtrip
found 4 hours ago
CLT
Charlotte-Douglas Intl.
OWB
Owensboro-Daviess County Regional
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
ORD
O'Hare Intl.
PAH
Barkley Regional
$199 Roundtrip, found 7 hours ago
$199
Roundtrip
found 7 hours ago
MCI
Kansas City Intl.
PAH
Barkley Regional
$274 Roundtrip, found 13 hours ago
$274
Roundtrip
found 13 hours ago
MCI
Kansas City Intl.
EVV
Evansville Regional
$367 Roundtrip, found 2 days ago
$367
Roundtrip
found 2 days ago
JFK
John F. Kennedy Intl.
OWB
Owensboro-Daviess County Regional
$414 Roundtrip, found 1 day ago
$414
Roundtrip
found 1 day ago
ORD
O'Hare Intl.
EVV
Evansville Regional
$415 Roundtrip, found 2 days ago
$415
Roundtrip
found 2 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ORD | Marion | July 23 to July 23 | $173 |
| ORD | Owensboro | July 29 to August 4 | $178 |
| ORD | West Paducah | August 1 to August 5 | $199 |
| DFW | West Paducah | October 2 to October 16 | $294 |
| SEA | West Paducah | September 5 to September 12 | $346 |
| IAD | Evansville | July 29 to August 1 | $392 |
| DFW | Evansville | October 15 to October 20 | $405 |
| DFW | Marion | August 27 to September 1 | $409 |
| ORD | Evansville | August 8 to August 12 | $415 |
| DFW | Owensboro | September 25 to September 27 | $476 |
| SAN | Evansville | September 24 to September 27 | $519 |
| SEA | Evansville | August 18 to August 23 | $539 |
| SAN | Owensboro | July 23 to July 27 | $681 |
| SEA | Marion | August 13 to August 19 | $712 |
| COS | West Paducah | July 31 to August 2 | $796 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ORD | Owensboro | July 12 to July 26 | $289 |
| ORD | Marion | July 12 to July 12 | $343 |
| COS | Evansville | July 11 to July 18 | $476 |
| ORD | West Paducah | July 12 to July 18 | $577 |
| DFW | Evansville | July 10 to July 11 | $641 |
Travelers ❤️ These Caldwell County 🏨

Kentucky Dam Village State Resort Park
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

Days Inn by Wyndham Madisonville
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

Pennyrile Forest State Resort Park
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
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Hotel Barkley
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
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.




