$89 Cheap flights to Grayson County

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Cheap flights to Grayson County from $89 One Way, $178 Round Trip

$178 return flights and $89 one-way flights to Grayson County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Sep 4 - Mon, Sep 7
ORD
Chicago
OWB
Owensboro
$178 Roundtrip, just found
$178
Roundtrip
just found
Select Contour Airlines flight, departing Fri, Sep 4 from Chicago to Owensboro, returning Mon, Sep 7, priced at $178 just found
Fri, Aug 21 - Sun, Aug 23
ORD
Chicago
OWB
Owensboro
$183 Roundtrip, found 7 hours ago
$183
Roundtrip
found 7 hours ago
Select Contour Airlines flight, departing Fri, Aug 21 from Chicago to Owensboro, returning Sun, Aug 23, priced at $183 found 7 hours ago
Thu, Jul 30 - Sun, Aug 2
CLT
Charlotte
OWB
Owensboro
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Thu, Jul 30 from Charlotte to Owensboro, returning Sun, Aug 2, priced at $188 found 1 day ago
Thu, Aug 13 - Mon, Aug 17
CLT
Charlotte
OWB
Owensboro
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Thu, Aug 13 from Charlotte to Owensboro, returning Mon, Aug 17, priced at $193 found 1 day ago
Fri, Jul 17 - Mon, Jul 20
CLT
Charlotte
OWB
Owensboro
$193 Roundtrip, found 13 hours ago
$193
Roundtrip
found 13 hours ago
Select Contour Airlines flight, departing Fri, Jul 17 from Charlotte to Owensboro, returning Mon, Jul 20, priced at $193 found 13 hours ago
Fri, Sep 4 - Mon, Sep 7
CLT
Charlotte
OWB
Owensboro
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Fri, Sep 4 from Charlotte to Owensboro, returning Mon, Sep 7, priced at $208 found 3 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
LGAOwensboroJuly 10 to July 12$591
BOSOwensboroJuly 12 to July 18$670
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Grayson County Accommodation Deals

Rough River Dam State Resort Park

Rough River Dam State Resort Park

3 out of 5
450 Lodge Rd Falls of Rough KY
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $110 total per night from Aug 2 to Aug 3
$110 total
Aug 2 - Aug 3
Total with taxes and fees
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 ...
9.2/10 Wonderful! (265 reviews)
"We love staying at rough river lodge. I wish they had small refrigerators in each room but other than that we love everything the lodge has to offer."

Reviewed on Jun 28, 2026

Opens in a new windowRough River Dam State Resort Park
The Getaway @ Nolin

The Getaway @ Nolin

Clarkson KY
Stay at this vacation home in Clarkson. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Anneta Community Park and Moutardier ...
9.6/10 Exceptional! (30 reviews)
"Very cute and charming property! We enjoyed the deck! Communication with the host was excellent. Thank you for a wonderful stay!"

Reviewed on Jul 4, 2026

Get rates
Opens in a new windowThe Getaway @ Nolin
Homestay on Main by Twin Lakes Creamery

Homestay on Main by Twin Lakes Creamery

3 out of 5
304 N Main St Leitchfield KY
$116 nightly
The price is $129 total per night from Jul 5 to Jul 6
$129 total
Jul 5 - Jul 6
Total with taxes and fees
Stay at this B&B in Leitchfield. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Historic Grayson County Courthouse and Logsdon Park ...
8.8/10 Excellent! (45 reviews)
"Very nice rooms with private bathroom"

Reviewed on May 23, 2026

Opens in a new windowHomestay on Main by Twin Lakes Creamery
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The Treehouse

The Treehouse

Leitchfield KY
$142 nightly
The price is $158 total per night from Jul 5 to Jul 6
$158 total
Jul 5 - Jul 6
Total with taxes and fees
Stay at this aparthotel in Leitchfield. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Historic Grayson County Courthouse ...
10/10 Exceptional! (31 reviews)
"Fantastic property and convenient to attractions. Will have to come back to explore the local town."

Reviewed on Jun 21, 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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Grayson County

End your search for discount fares on flights to Grayson County. Orbitz has all the best prices on Grayson County flights. With Orbitz, you can expect:

Cheap Deals on Flights to Grayson County

We offer big discounts and last-minute savings on Grayson County flights. We make it easy for you to research, plan, and book your flight to Grayson County — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

Travel Convenience on the Go

Get alerts, updates, or book your Grayson County flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Grayson County flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Grayson County flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Grayson County flights to the actual booking. If you want to cancel your flight to Grayson County, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Grayson County with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

Frequently asked questions

Which airlines fly to Grayson County?
Secure a fare with one of the 12 airlines that fly to Nashville Intl. Airport (BNA) and get set to embark on new adventures. This popular airport is a major entry point for Grayson County. When it's time to see this region, these top carriers will get you there:

  • Air Canada - 42 flights to Grayson County per month
  • WestJet - 20 flights to Grayson County per month
  • British Airways - 16 flights to Grayson County per month

How much is a flight to Grayson County?
Travelers from near and far picked up round-trip deals ranging between $178 and $670 this week. Arriving from Chicago (ORD)? The cheapest one-way tickets started at just $89.
How to book the cheapest flight to Grayson County?
With some of the most competitive flight deals around, you'll always bag a bargain with Orbitz. The following pointers will help you land cheap flights to Grayson County — and leave you with more cash to play with:

  • Taking off from or landing at other airports may save you money. Type in your preferred departure and arrival airports. Next, select the 'Nearby airports' function below the form fields to see your options.
  • Also, click on the 'Show flexible dates' option to view the fares on days either side of your chosen departure. It's possible to pick up cheaper flight deals if your itinerary is flexible.
  • You can also use the 'Show options' link to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you want to fly.
  • Reserve your seat as soon as you've worked out your travel dates. While it does happen now and then, flights rarely get more affordable as your departure date gets closer.
  • Save big on your vacation by combining your flights, hotels and car rentals into an Orbitz package deal. Your wallet will thank you for it.
  • If possible, avoid traveling in the most popular seasons. Airfares usually surge during summer, school breaks and other vacation periods like Thanksgiving and Christmas.

What is the best time to book a flight to Grayson County?
Generally speaking, January is the cheapest time to book your airfare. This is closely followed by February and August. Keep this in mind while you look for a cheap flight to Grayson County.
What day of the week is the cheapest to book a flight to Grayson County?
When it comes to cheap flights to Grayson County, the best days to make a booking are generally Tuesdays, Wednesdays and Saturdays. An unbeatable flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Grayson County?
Based on Orbitz data from 2020, Monday is usually the best day to get cheap flights to Grayson County. Tuesday also has budget-friendly fares whereas Saturday has the highest ticket rates. Even though flying out at the weekend can be more suitable, you'll have more cash in your pocket to play with if you set off earlier in the week.
What is the cheapest month to fly to Grayson County?
To pick up cheap flights to Grayson County, pack your bags and depart in August. Orbitz data has found that this is generally a great month to save serious money on your fare. If you want to jet to Grayson County in June, be aware that this is the most expensive time of year to travel.
Which airlines allow free cancellation?
Orbitz makes it a cinch to find airlines that offer flexibility. Simply click on "Filter by flexible change policies" when searching for your Grayson County flights and bada bing! We'll show you options that include free cancellation within 24 hours of booking, no change fees and of course, the very best price.
What do I need for the flight to Grayson County?
Nothing's more fun than jetting off on an adventure, but it pays to be prepared. The following useful tips will help get your journey off to a smooth start:

  • Before you board the plane, you'll need to present proof of identification, such as your passport. You'll also need your ticket. If you're traveling with children, check with your airline about which documents they require — if any.
  • Make time fly by even faster on your short flight by packing the right things. Think snacks, a water bottle and entertainment. If you want your trip to Grayson County to go nice and quietly, throw some noise-canceling headphones in your bag as well.
  • Even if you're flying in the height of summer, take a sweater on board with you. Airplane cabins can get downright chilly.

How do I get cheap first-class/business deals to Grayson County?
If you think a business or first-class ticket is way out of your reach, think again. Here are some tips to help you land a premium flight to Grayson County for less:

  • Flexibility isn't just for the gym. Leave some room to move around your travel dates so you can snap up cheaper airfares when a huge sale drops.
  • A lot of low-cost carriers these days have outstanding business or premium-class seating that doesn't cost an arm and a leg.
  • Make the most of your airline's loyalty program and upgrade your seat. You can also bid for an upgrade in an online auction if available.

What is the best time to go to Grayson County?
Anytime is a great time to vacation in Grayson County, though April, May and June are the most popular months. Like most places in the Northern Hemisphere, summer kicks off June 20. If you'd like to get around in a light shirt than a winter coat, this time of the year may be perfect for you. Expect average daily highs of 85 ºF and nightly lows around 65 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.