Cheap Flights to Webster County from $53 (2026/2027)

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How Much Does it Cost To Fly To Webster County?

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

Sat, Aug 22 - Sat, Aug 29
MCO
Orlando Intl.
EVV
Evansville Regional
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Aug 22 from Orlando Intl. to Evansville Regional, returning Sat, Aug 29, priced at $107 found 1 day ago
Thu, Jul 23 - Wed, Jul 29
ORD
O'Hare Intl.
OWB
Owensboro-Daviess County Regional
$178 Roundtrip, found 23 hours ago
$178
Roundtrip
found 23 hours ago
Select Contour Airlines flight, departing Thu, Jul 23 from O'Hare Intl. to Owensboro-Daviess County Regional, returning Wed, Jul 29, priced at $178 found 23 hours ago
Wed, Sep 9 - Wed, Sep 16
CLT
Charlotte-Douglas Intl.
OWB
Owensboro-Daviess County Regional
$188 Roundtrip, found 22 hours ago
$188
Roundtrip
found 22 hours ago
Select Contour Airlines flight, departing Wed, Sep 9 from Charlotte-Douglas Intl. to Owensboro-Daviess County Regional, returning Wed, Sep 16, priced at $188 found 22 hours ago
Fri, Oct 23 - Mon, Oct 26
CLE
Hopkins Intl.
EVV
Evansville Regional
$367 Roundtrip, found 2 days ago
$367
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 23 from Hopkins Intl. to Evansville Regional, returning Mon, Oct 26, priced at $367 found 2 days ago
Wed, Sep 30 - Sat, Oct 10
PBI
Palm Beach Intl.
EVV
Evansville Regional
$379 Roundtrip, found 2 days ago
$379
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Sep 30 from Palm Beach Intl. to Evansville Regional, returning Sat, Oct 10, priced at $379 found 2 days ago
Wed, Jul 29 - Sat, Aug 1
IAD
Washington Dulles Intl.
EVV
Evansville Regional
$392 Roundtrip, found 3 days ago
$392
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jul 29 from Washington Dulles Intl. to Evansville Regional, returning Sat, Aug 1, priced at $392 found 3 days ago
Sat, Aug 8 - Wed, Aug 12
ORD
O'Hare Intl.
EVV
Evansville Regional
$415 Roundtrip, found 5 days ago
$415
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Aug 8 from O'Hare Intl. to Evansville Regional, returning Wed, Aug 12, priced at $415 found 5 days ago
Thu, Aug 6 - Thu, Aug 13
LGA
LaGuardia
OWB
Owensboro-Daviess County Regional
$416 Roundtrip, found 1 day ago
$416
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Aug 6 from LaGuardia to Owensboro-Daviess County Regional, returning Thu, Aug 13, priced at $416 found 1 day ago
Thu, Sep 17 - Thu, Sep 24
IAD
Washington Dulles Intl.
OWB
Owensboro-Daviess County Regional
$416 Roundtrip, found 2 days ago
$416
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Sep 17 from Washington Dulles Intl. to Owensboro-Daviess County Regional, returning Thu, Sep 24, priced at $416 found 2 days ago
Thu, Aug 6 - Thu, Aug 13
EWR
Newark Liberty Intl. Airport
OWB
Owensboro-Daviess County Regional
$416 Roundtrip, found 1 day ago
$416
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Aug 6 from Newark Liberty Intl. Airport to Owensboro-Daviess County Regional, returning Thu, Aug 13, priced at $416 found 1 day ago
Thu, Aug 20 - Sun, Aug 23
LGA
LaGuardia
EVV
Evansville Regional
$457 Roundtrip, found 6 days ago
$457
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Aug 20 from LaGuardia to Evansville Regional, returning Sun, Aug 23, priced at $457 found 6 days ago
OriginDestinationTravel DatesFlights From*
ORDOwensboroJuly 22 to July 27$178
CLTOwensboroJuly 23 to July 27$188
ATLEvansvilleAugust 2 to August 10$265
IADEvansvilleJuly 29 to August 1$392
ORDEvansvilleAugust 8 to August 12$415
IADOwensboroSeptember 17 to September 24$416
TPAEvansvilleJuly 23 to July 26$467
CLTEvansvilleOctober 1 to October 10$469
DFWEvansvilleAugust 8 to August 23$495
DFWOwensboroAugust 3 to August 7$504
SANEvansvilleSeptember 24 to September 27$519
SEAEvansvilleAugust 18 to August 23$539
SANOwensboroAugust 6 to August 10$565
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDOwensboroJuly 11 to July 12$357
COSEvansvilleJuly 11 to July 18$478
*Prices include taxes and fees

Best Webster County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn Henderson-Evansville South
2.5-star property

Sleep Inn Henderson-Evansville South

Jul 20 - Jul 24

4 night stay

Manchester (MHT) to Evansville (EVV)

American Airlines • Non-stop roundtrip • Coach
Price was $1,061, price is now $997 per person
$997
per person
found 23 hours ago
Holiday Inn Express Evansville West by IHG
2.5-star property

Holiday Inn Express Evansville West by IHG

Jul 20 - Jul 24

4 night stay

Manchester (MHT) to Evansville (EVV)

American Airlines • Non-stop roundtrip • Coach
Price was $1,154, price is now $1,074 per person
$1,074
per person
found 23 hours ago
Comfort Inn Henderson - Evansville South
2.5-star property

Comfort Inn Henderson - Evansville South

Jul 20 - Jul 24

4 night stay

Manchester (MHT) to Evansville (EVV)

American Airlines • Non-stop roundtrip • Coach
Price was $1,080, price is now $1,013 per person
$1,013
per person
found 23 hours ago
Don't see what you're looking for?
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Travelers ❤️ These Webster County 🏨

Over Yonder!!

Over Yonder!!

Sebree KY
Stay at this vacation home in Sebree. Enjoy patios, an in-room coffeemaker, and air conditioning.
10/10 Exceptional! (12 reviews)
"This cabin was perfect for our stay. The host had everything we needed to be able to relax, let the kids play, and enjoy meals as a family despite being away from home. It was a beautiful property and we would definitely stay again!"

Reviewed on Jun 3, 2026

Opens in a new windowOver Yonder!!
Greenfield Inn & Suites Owensboro, KY Airport

Greenfield Inn & Suites Owensboro, KY Airport

2.5 out of 5
3220 W Parrish Ave Owensboro KY
Book a stay at this business-friendly hotel in Owensboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Western Kentucky Botanical Garden and Owensboro Sportscenter are located nearby.
8.6/10 Excellent! (1,007 reviews)
"Very clean well kept - whole place smells good .Breakfast was good also. Honestly its too cheap for accommodations would recommend to anyone.."

Reviewed on Jul 5, 2026

Opens in a new windowGreenfield Inn & Suites Owensboro, KY Airport
Wingate by Wyndham Owensboro

Wingate by Wyndham Owensboro

3 out of 5
51 Bon Harbor Hls Owensboro KY
Book a stay at this business-friendly hotel in Owensboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Western Kentucky Botanical Garden and Ben Hawes State Park are located nearby.
7.6/10 Good! (868 reviews)
"We noticed dead bugs around the pool. When we took our grandchildren down for breakfast it was obvious that the food had been sitting in the warming tray had been there for an extended time. The biscuits were not edible they were extremely hard. We found it very disturbing when the individual tending ..."

Reviewed on Jun 30, 2026

Opens in a new windowWingate by Wyndham Owensboro
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Days Inn by Wyndham Madisonville

Days Inn by Wyndham Madisonville

2 out of 5
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! (939 reviews)
"Propiedad oscura , húmeda y todo antiguo por el precio que tiene no lo recomiendo nunca"

Reviewed on Jul 5, 2026

Opens in a new windowDays Inn by Wyndham Madisonville
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 Webster County?
Travelers snapped up a roundtrip flight to Webster County for as little as $107 within the last seven days. If you spot a great bargain, get in quick. Cheap deals don't wait around for long! This price was available on Travelocity for flights to Webster County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Webster County?
Pack your suitcase and take off with any of the 20 airline companies that operate flights to Webster County. Secure a seat with the leading carrier, Southwest Airlines. It has approximately 3,614 flights a month to Providence, Webster County's primary city, so finding the right fare should be a snap.
What is the cheapest month to fly to Webster County?
For the best shot at securing an excellent flight deal, organize your break during August. Based on Travelocity's direct flight demand from January to December last year, it's the most affordable time to fly to Webster County.
How can I check my flight status to Webster County?
Receive updates on your flight to Webster County, make changes to your journey and loads more from our "Trips" customer portal. Found at the top of the Travelocity homepage, it's your one-stop shop for viewing and managing your bookings. All you have to do is sign in or create a new account in seconds. Savvy wanderers can also take advantage of the Travelocity app. You'll get real-time trip updates, along with the ability to view and lock in hotels, flights and rental cars while you're out and about. If you have friends or family flying with you, it's also a great way to share travel details with each other.
How do I find the best deals on flights to Webster County?
You'll always find an amazing deal with Travelocity — our "Flexible dates" function makes it a lot easier. Enter your travel dates, then click on the flexible dates box above your search results to see the prices for surrounding days. $107 was the lowest price for a roundtrip flight to Webster County in the last seven days. 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 Webster County with Travelocity?
Check out cheap flights to Webster County with Travelocity and begin packing for your next adventure. With 24/7 customer support during all stages of your trip and a Price Match Guarantee, we take the hassle out of finding cheap family flights, places to stay, activities and more. Snap up a top deal today and gear up for an epic adventure.
What are the most popular flight routes to Webster County?
As a leading destination for travelers, it's a cinch to find flights to Webster County. Take a peek at this list of popular routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Evansville Regional Airport (EVV) - 693 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Evansville Regional Airport (EVV) - 580 flights a month.
  • Dallas, TX (DFW-Dallas-Fort Worth Intl.) to Evansville Regional Airport (EVV) - 424 flights a month.

How much is a flight to Webster County on average?
Travelers have booked roundtrip flights to Webster County for between $107 and $565 with Travelocity in the last seven days. Whether you're looking to fly economy or first class, we'll help you get an incredible deal. 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 Webster County?
To get a feel for the average airborne time of a direct flight to Webster County, take a look at these popular routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Evansville Regional Airport (EVV) - 1 hour and 14 minutes
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Evansville Regional Airport (EVV) - 1 hour and 22 minutes
  • Dallas, TX (DFW-Dallas-Fort Worth Intl.) to Evansville Regional Airport (EVV) - 1 hour and 51 minutes

What can I expect on a flight to Webster County?
That depends on a couple of factors. Is your flight to Webster County long or short? Will you fly with a full-service airline or a low-cost option? These things will affect your onboard experience. If you're flying long haul, most airlines include drinks, hot meals and entertainment. Budget carriers are a smart option when it comes to cheap flights for family vacations or shorter trips. That said, they often won't have the same inclusions as a full-service carrier.