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

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Mammoth Cave National Park

Leitchfield

Flights
Leitchfield

How Much Does it Cost To Fly To Grayson County?

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

Tue, Jul 14 - Tue, Jul 14
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$177 Roundtrip, found 3 days ago
$177
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Tue, Jul 14 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Tue, Jul 14, priced at $177 found 3 days ago
Thu, Jun 4 - Mon, Jun 8
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$178 Roundtrip, found 17 hours ago
$178
Roundtrip
found 17 hours ago
Select Contour Airlines flight, departing Thu, Jun 4 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Mon, Jun 8, priced at $178 found 17 hours ago
Sat, Jun 20 - Sun, Jun 21
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$183 Roundtrip, found 6 hours ago
$183
Roundtrip
found 6 hours ago
Select Contour Airlines flight, departing Sat, Jun 20 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Sun, Jun 21, priced at $183 found 6 hours ago
Thu, Jul 23 - Sun, Jul 26
CLT
Charlotte-Douglas Intl.
OWB
Owensboro-Daviess County Regional
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Thu, Jul 23 from Charlotte-Douglas Intl. to Owensboro-Daviess County Regional, returning Sun, Jul 26, priced at $188 found 3 days ago
Fri, Jun 12 - Sun, Jun 14
CLT
Charlotte-Douglas Intl.
OWB
Owensboro-Daviess County Regional
$193 Roundtrip, found 4 hours ago
$193
Roundtrip
found 4 hours ago
Select Contour Airlines flight, departing Fri, Jun 12 from Charlotte-Douglas Intl. to Owensboro-Daviess County Regional, returning Sun, Jun 14, priced at $193 found 4 hours ago
Fri, Jun 5 - Thu, Jun 11
CLT
Charlotte-Douglas Intl.
OWB
Owensboro-Daviess County Regional
$193 Roundtrip, found 2 hours ago
$193
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Fri, Jun 5 from Charlotte-Douglas Intl. to Owensboro-Daviess County Regional, returning Thu, Jun 11, priced at $193 found 2 hours ago
Thu, Jul 9 - Sun, Jul 12
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Thu, Jul 9 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Sun, Jul 12, priced at $203 found 1 day ago
Wed, Jun 17 - Mon, Jun 22
CLT
Charlotte-Douglas Intl.
OWB
Owensboro-Daviess County Regional
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Wed, Jun 17 from Charlotte-Douglas Intl. to Owensboro-Daviess County Regional, returning Mon, Jun 22, priced at $234 found 4 days ago
OriginDestinationTravel DatesFlights From*
DFWOwensboroJune 7 to June 29$1,039
*Prices include taxes and fees

Best Grayson County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Louisville Airport South by IHG
3.0-star property

Holiday Inn Louisville Airport South by IHG

Jul 5 - Jul 8

3 night stay

Boston (BOS) to Louisville (SDF)

Delta • Roundtrip • Coach
Price was $854, price is now $624 per person
$624
per person
found 7 hours ago
Cottonwood Airport & Expo Hotel Louisville
3.5-star property

Cottonwood Airport & Expo Hotel Louisville

Jul 5 - Jul 8

3 night stay

Boston (BOS) to Louisville (SDF)

Delta • Roundtrip • Coach
Price was $940, price is now $671 per person
$671
per person
found 7 hours ago
Louisville Marriott Downtown
4.0-star property

Louisville Marriott Downtown

Jul 5 - Jul 8

3 night stay

Boston (BOS) to Louisville (SDF)

Delta • Roundtrip • Coach
Price was $1,014, price is now $735 per person
$735
per person
found 7 hours ago
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Travelers ❤️ These Grayson County 🏨

Rough River Dam State Resort Park

Rough River Dam State Resort Park

3 out of 5
450 Lodge Rd Falls of Rough KY
Book a stay at this beach hotel in Falls of Rough. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Rough River Dam State Resort Park and Rough River Lake are located nearby.
9.2/10 Wonderful! (253 reviews)
"The staff was very nice.. our room was covered in spider webs and giant wolf spiders. The phone didnt work to call front desk. We asked to switch rooms which they accommodated quickly. That room had even more spiders and large webs.."

Reviewed on May 22, 2026

Opens in a new windowRough River Dam State Resort Park
Georgia’s Landing-NEWLY REMODELED-Waterfront-Hot tub-Luxury and peaceful

Georgia’s Landing-NEWLY REMODELED-Waterfront-Hot tub-Luxury and peaceful

Clarkson KY
Book a stay at this family-friendly vacation home in Clarkson. Enjoy free WiFi, a garden, and laundry facilities. Popular attraction Anneta Community Park is located nearby.
10/10 Exceptional! (195 reviews)
"the place was wonderful and clean. This place I would stay again we had so much fun and the rooms were great the beds comfortable and every were you went was quiet and the view was exceptional. Thank you so much for letting us stay here with our family and making family dreams come true. Yours truly ..."

Reviewed on May 6, 2026

Opens in a new windowGeorgia’s Landing-NEWLY REMODELED-Waterfront-Hot tub-Luxury and peaceful
Log Cabin Nolin Lake

Log Cabin Nolin Lake

Clarkson KY
Stay at this vacation home in Clarkson. Enjoy laundry facilities, in-room washers/dryers, and in-room fireplaces. Popular attractions Anneta Community Park and Moutardier Marina are located nearby.
8.6/10 Excellent! (143 reviews)
"The cabin was cozy and provided plenty of room. It does not have a lake view. We tried to walk to where we thought the lake might be, but were unsuccessful. The kitchen, living room, and bathroom were clean, but bedrooms had mouse and squirrel dropping on bedding. We had to wash bedding before we ..."

Reviewed on Jan 3, 2026

Opens in a new windowLog Cabin Nolin Lake
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The Treehouse

The Treehouse

Leitchfield KY
Stay at this aparthotel in Leitchfield. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Historic Grayson County Courthouse and Logsdon Park West are located nearby.
10/10 Exceptional! (26 reviews)
"This is a very nice property in small-town Kentucky. It's clean, easy to access up one flight of outside stairs, has good parking, and is private. Requirements for checking out are easily accomplished. Recommend."

Reviewed on Apr 22, 2026

Opens in a new windowThe Treehouse
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 Grayson County?
In the last seven days, the cheapest roundtrip flight to Grayson County cost $177 on our site. Look through our unbeatable deals, secure your booking and start planning for your next travel adventure. This price was available on Travelocity for flights to Grayson County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Grayson County?
There are 15 airlines offering flights to Grayson County. If you're planning a trip to Leitchfield, opt for American Airlines. This top-rated carrier operates around 680 services a month to Grayson County's major city.
What is the cheapest month to fly to Grayson County?
Based on Travelocity's direct return flight demand from January to December last year, July is the cheapest month to journey to Grayson County. Look for flights across this month and lock in a terrific deal today.
How can I check my flight status to Grayson County?
Go to Travelocity's customer portal, Trips. You'll find all things related to your flight to Grayson County here, including important information about flight delays, gate changes and more. Keep an eye out for Trips at the top right of the Travelocity homepage. Just create your free acount and get the answers to your questions. You can also access your itinerary on the move and get real-time trip updates with the Travelocity app. All your itineraries are in one place, so it's easy to share details with any members of your family flying with you.
How do I find the best deals on flights to Grayson County?
One easy way to get your hands on the best deal is to be flexible with your travel dates. Start by searching for your flight to Grayson County, then tap on the "Flexible dates" box above the results. This will show you prices for the surrounding dates. Want another handy tip? Book ahead of time. To give you an idea of fares, $177 was the cheapest price for a return flight to Grayson County in the last seven days 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 Grayson County with Travelocity?
If you're searching for cheap flights to Grayson County, you'll uncover some great deals with Travelocity. From cheap family flights on low-cost airlines to flexible tickets, we can help you. Enjoy a hassle-free break with our 24/7 Virtual Agent online chat, Price Match Guarantee and free cancellation policies with most hotels. Start planning your itinerary and prepare to step onboard a plane to this interesting destination.
What are the most popular flight routes to Grayson County?
To help you find flights to Grayson County, here's a list of some of the leading 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 Grayson County on average?
Based on prices found over the last seven days, roundtrip flights to Grayson County were between $177 and $1,039. Whenever you're ready to take off, Travelocity will help you find a fare that won't blow 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 Grayson County?
Have a look at these favorite routes to get an idea on how long you'll be airborne on a direct flight to Grayson County:

  • 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 Grayson County?
That mainly depends on where you're traveling from and which airline you're flying with. Chances are you'll find all sorts of flights to Grayson County, from business class journeys to cheap flights for family vacations. If you're flying long haul, your airline will generally offer hot meals and entertainment as well as games to amuse the kids.