$89 Cheap flights to Grayson County

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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.

Mon, Aug 24 - Thu, Aug 27
ORD
Chicago
OWB
Owensboro
$178 Roundtrip, found 7 hours ago
$178
Roundtrip
found 7 hours ago
Select Contour Airlines flight, departing Mon, Aug 24 from Chicago to Owensboro, returning Thu, Aug 27, priced at $178 found 7 hours ago
Fri, Aug 21 - Tue, Aug 25
ORD
Chicago
OWB
Owensboro
$181 Roundtrip, found 3 hours ago
$181
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Fri, Aug 21 from Chicago to Owensboro, returning Tue, Aug 25, priced at $181 found 3 hours ago
Fri, Oct 9 - Sun, Oct 11
CLT
Charlotte
OWB
Owensboro
$188 Roundtrip, found 4 days ago
$188
Roundtrip
found 4 days ago
Select Contour Airlines flight, departing Fri, Oct 9 from Charlotte to Owensboro, returning Sun, Oct 11, priced at $188 found 4 days ago
Thu, Aug 20 - Mon, Aug 24
CLT
Charlotte
OWB
Owensboro
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Thu, Aug 20 from Charlotte to Owensboro, returning Mon, Aug 24, priced at $191 found 1 day ago
Fri, Sep 4 - Sun, Sep 6
CLT
Charlotte
OWB
Owensboro
$191 Roundtrip, found 1 hour ago
$191
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Fri, Sep 4 from Charlotte to Owensboro, returning Sun, Sep 6, priced at $191 found 1 hour ago
Mon, Aug 17 - Wed, Aug 19
ORD
Chicago
OWB
Owensboro
$211 Roundtrip, found 6 days ago
$211
Roundtrip
found 6 days ago
Select Contour Airlines flight, departing Mon, Aug 17 from Chicago to Owensboro, returning Wed, Aug 19, priced at $211 found 6 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
LAXOwensboroAugust 8 to August 10$1,820
*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 9 to Aug 10
$110 total
Aug 9 - Aug 10
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! (272 reviews)
"I enjoyed my stay very much so...."

Reviewed on Jul 28, 2026

Opens in a new windowRough River Dam State Resort Park
Falls of Rough Motel

Falls of Rough Motel

2 out of 5
13689 Falls of Rough Rd Falls of Rough KY
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $104 total per night from Aug 9 to Aug 10
$104 total
Aug 9 - Aug 10
Total with taxes and fees
Stay at this motel in Falls of Rough. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Rough River Dam State Resort Park and Rough ...
Opens in a new windowFalls of Rough Motel
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! (32 reviews)
"This was a perfect little place to stay for quick weekend! It was clean and had everything we needed!! The host answered us promptly!"

Reviewed on Aug 2, 2026

Get rates
Opens in a new windowThe Getaway @ Nolin
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Homestay on Main by Twin Lakes Creamery

Homestay on Main by Twin Lakes Creamery

3 out of 5
304 N Main St Leitchfield KY
$104 nightly
The price is $115 total per night from Aug 9 to Aug 10
$115 total
Aug 9 - Aug 10
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! (50 reviews)
"Outside grounds were in terrible shape but the worst part was the kitchen. We were given kitchen privileges and when we tried to use it there were two sinks full of dirty glasses and cups, shoes and fly poison on the counter top and a very filthy stove. My wife needs a special diet which we could ..."

Reviewed on Aug 6, 2026

Opens in a new windowHomestay on Main by Twin Lakes Creamery
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

Save money on your flights to Grayson County as well as on hotel and car packages.

 

Free Fees

Snap up cheap Grayson County flights at Orbitz, and pay no booking fees. We also don’t charge fees when your plans change or are cancelled. While you’re there, check out our low fare deals on flights to other locations besides flights to Grayson County.

Everyday Is a Great Day to Save Even More

Get bonus points from Orbitz, the best discount travel planner in the business. Use your Orbitz Visa to take advantage of sales on Grayson County flights, or pile on points by using it for gas, groceries, and other everyday goods and services. Pack your wallet with even more savings using our cutting-edge suite of mobile tools.

Mix and Match

At Orbitz, we turned a great idea from the world of fashion into another way for you to save money. When you shop our low cost tickets on flights to any destination, don’t be afraid to mix and match different airlines for maximum savings on your Grayson County flights air ticket. Save more on air travel every day in every way at Orbitz.

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 $1,820 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.