$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.

Tue, Jul 7 - Sat, Jul 11
ORD
Chicago
OWB
Owensboro
$178 Roundtrip, found 14 hours ago
$178
Roundtrip
found 14 hours ago
Select Contour Airlines flight, departing Tue, Jul 7 from Chicago to Owensboro, returning Sat, Jul 11, priced at $178 found 14 hours ago
Thu, Aug 6 - Mon, Aug 10
ORD
Chicago
OWB
Owensboro
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Thu, Aug 6 from Chicago to Owensboro, returning Mon, Aug 10, priced at $183 found 1 day ago
Thu, Sep 10 - Mon, Sep 14
CLT
Charlotte
OWB
Owensboro
$188 Roundtrip, found 9 hours ago
$188
Roundtrip
found 9 hours ago
Select Contour Airlines flight, departing Thu, Sep 10 from Charlotte to Owensboro, returning Mon, Sep 14, priced at $188 found 9 hours ago
Fri, Jul 24 - Wed, Jul 29
BOI
Boise
OWB
Owensboro
$834 Roundtrip, found 1 day ago
$834
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Fri, Jul 24 from Boise to Owensboro, returning Wed, Jul 29, priced at $834 found 1 day ago
Tue, Aug 11 - Fri, Aug 14
FLL
Fort Lauderdale
OWB
Owensboro
$863 Roundtrip, found 11 hours ago
$863
Roundtrip
found 11 hours ago
Select Alaska Airlines flight, departing Tue, Aug 11 from Fort Lauderdale to Owensboro, returning Fri, Aug 14, priced at $863 found 11 hours ago
Thu, Sep 17 - Sun, Sep 20
BWI
Baltimore
OWB
Owensboro
$948 Roundtrip, found 19 hours ago
$948
Roundtrip
found 19 hours ago
Select Alaska Airlines flight, departing Thu, Sep 17 from Baltimore to Owensboro, returning Sun, Sep 20, priced at $948 found 19 hours ago
Loading

Deals For This Weekend's Flights

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 Jun 21 to Jun 22
$110 total
Jun 21 - Jun 22
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! (260 reviews)
"We love our stay it was clean in the beds was nice they make you feel at home. The pool was fun and clean. There’s a lot to do bunch of activities."

Reviewed on Jun 15, 2026

Opens in a new windowRough River Dam State Resort Park
The Treehouse

The Treehouse

Leitchfield KY
$150 nightly
The price is $167 total per night from Jul 13 to Jul 14
$167 total
Jul 13 - Jul 14
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! (30 reviews)
"We loved our stay in The Treehouse. So nice and clean! Great proximity to Mammoth Cave National Park and a fantastic coffee shop nearby! The hosts were hospitable with good communication!"

Reviewed on Jun 10, 2026

Opens in a new windowThe Treehouse
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! (27 reviews)
"Good lake house"

Reviewed on Jun 10, 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 Jun 22 to Jun 23
$115 total
Jun 22 - Jun 23
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
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

Reach your destination without breaking your budget by booking your flights to Grayson County using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Grayson County Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Grayson County flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Grayson County. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Grayson County, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Grayson County flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

.

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 $948 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.