$52 Cheap flights to Webster County

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Cheap flights to Webster County from $52 One Way, $84 Round Trip

$84 return flights and $52 one-way flights to Webster 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.

Thu, Aug 20 - Sun, Aug 23
SFB
Orlando
EVV
Evansville
$84 Roundtrip, found 9 hours ago
$84
Roundtrip
found 9 hours ago
Select Allegiant Air flight, departing Thu, Aug 20 from Orlando to Evansville, returning Sun, Aug 23, priced at $84 found 9 hours ago
Sat, Aug 15 - Sat, Aug 22
MCO
Orlando
EVV
Evansville
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Aug 15 from Orlando to Evansville, returning Sat, Aug 22, priced at $130 found 4 days ago
Fri, Sep 11 - Sun, Sep 13
ORD
Chicago
OWB
Owensboro
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Fri, Sep 11 from Chicago to Owensboro, returning Sun, Sep 13, priced at $178 found 2 hours ago
Sat, Jul 25 - Sun, Jul 26
ORD
Chicago
OWB
Owensboro
$183 Roundtrip, found 3 hours ago
$183
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Sat, Jul 25 from Chicago to Owensboro, returning Sun, Jul 26, priced at $183 found 3 hours ago
Sun, Oct 11 - Thu, Oct 15
PIE
St. Petersburg
EVV
Evansville
$186 Roundtrip, found 4 hours ago
$186
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Sun, Oct 11 from St. Petersburg to Evansville, returning Thu, Oct 15, priced at $186 found 4 hours ago
Fri, Sep 11 - Sun, Sep 13
CLT
Charlotte
OWB
Owensboro
$188 Roundtrip, found 4 hours ago
$188
Roundtrip
found 4 hours ago
Select Contour Airlines flight, departing Fri, Sep 11 from Charlotte to Owensboro, returning Sun, Sep 13, priced at $188 found 4 hours ago
Wed, Aug 26 - Mon, Aug 31
CLT
Charlotte
OWB
Owensboro
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Wed, Aug 26 from Charlotte to Owensboro, returning Mon, Aug 31, priced at $193 found 1 day ago
Thu, Jul 23 - Mon, Jul 27
CLT
Charlotte
OWB
Owensboro
$193 Roundtrip, just found
$193
Roundtrip
just found
Select Contour Airlines flight, departing Thu, Jul 23 from Charlotte to Owensboro, returning Mon, Jul 27, priced at $193 just found
Fri, Jul 24 - Tue, Jul 28
ORD
Chicago
OWB
Owensboro
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Fri, Jul 24 from Chicago to Owensboro, returning Tue, Jul 28, priced at $213 found 1 day ago
Fri, Aug 14 - Sat, Aug 15
EWR
New York
EVV
Evansville
$356 Roundtrip, found 6 hours ago
$356
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Fri, Aug 14 from New York to Evansville, returning Sat, Aug 15, priced at $356 found 6 hours ago
Thu, Aug 13 - Sat, Aug 15
EWR
New York
OWB
Owensboro
$375 Roundtrip, found 6 hours ago
$375
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Thu, Aug 13 from New York to Owensboro, returning Sat, Aug 15, priced at $375 found 6 hours ago
Wed, Oct 7 - Wed, Oct 14
SLC
Salt Lake City
EVV
Evansville
$419 Roundtrip, found 6 hours ago
$419
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Wed, Oct 7 from Salt Lake City to Evansville, returning Wed, Oct 14, priced at $419 found 6 hours ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
CLTOwensboroJuly 17 to July 20$234
ORDOwensboroJuly 19 to July 23$290
PIEEvansvilleJuly 19 to July 26$310
DFWEvansvilleJuly 19 to July 25$604
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Webster County Accommodation Deals

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

Get rates
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
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $97 total per night from Jul 12 to Jul 13
$97 total
Jul 12 - Jul 13
Total with taxes and fees
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 ...
8.6/10 Excellent! (1,013 reviews)
"Staff were rushing and banging on the door when I asked for a late check out. When somebody came back for the THIRD time, I was told that I had 10 minutes before they were going to charge my card for another day. When I was leaving, I asked the woman at the front desk about checking my room so that ..."

Reviewed on Jul 9, 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
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $82 total per night from Jul 23 to Jul 24
$82 total
Jul 23 - Jul 24
Total with taxes and fees
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 ...
7.6/10 Good! (870 reviews)
"The sheets and bed spread were dirty, the person at the front desk wanted us to change them! The tv also won’t work."

Reviewed on Jul 6, 2026

Opens in a new windowWingate by Wyndham Owensboro
Save an average of 15% on thousands of hotels when you're signed in
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Days Inn by Wyndham Madisonville

Days Inn by Wyndham Madisonville

2 out of 5
1900 Lantaff Blvd Madisonville KY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $99 total per night from Aug 1 to Aug 2
$99 total
Aug 1 - Aug 2
Total with taxes and fees
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 ...
7/10 Good! (940 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.

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

Webster County

Reach your destination without breaking your budget by booking your flights to Webster 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 Webster County Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Webster 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 Webster 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 Webster 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 Webster 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.

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Frequently asked questions

Which airlines fly to Webster County?
You're spoiled for choice with 24 popular airlines that jet into Evansville Regional Airport (EVV). Compare the available fares and grab a cheap flight to Webster County with any one of these domestic carriers:

  • American Airlines - 73 flights to Webster County per month
  • Delta - 22 flights to Webster County per month
  • Allegiant Air - 0 flights to Webster County per month

How much is a flight to Webster County?
Plenty of excellent deals were going begging this week, with return flights to Webster County ranging between $84 and $604. But it was jet-setters beginning their trip from Orlando (SFB) who bagged the best bargains. One-way tickets to Webster County started at a low $52.
How to book the cheapest flight to Webster County?
With some of the best flight deals around, bagging a bargain is easy with Orbitz. The following handy hints will help you find cheap flights to Webster County — and leave you with cash to spare:

  • Depending on where you're taking off from, select the 'Nearby airports' function (located under the departure and arrival form fields). In some cases, other departure points will offer better prices on fares.
  • If you're flexible with your travel itinerary, click on the 'Show flexible dates' option. It'll show the flight deals for the days before and after your selected departure. Airfares often vary depending on what day it is.
  • To filter your results, hit 'Show options.' You can search based on seating class, airlines, nonstop flights and refundable flights. You can also choose your preferred departure and arrival times under 'Sort & Filter' to the left.
  • If you know your travel dates, don't waste time booking your flight. Ticket prices normally increase as the departure date gets closer.
  • Bundle your flights, hotels and car rentals into an impressive package deal. Save your money for things you're really excited about, like exploring every corner of Webster County.
  • If possible, avoid flying in the busy season. Airfares are often at their highest during school breaks, summer and around other vacation times like Easter and Christmas.

What is the best time to book a flight to Webster County?
If your schedule allows, purchase your flights to Webster County in January. This is the best month to reserve low airfares, followed by February and August. With a bit of organizing, you're guaranteed to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Webster County?
When it comes to cheap airfares to Webster County, the best days to book are generally Tuesdays, Wednesdays and Saturdays. A rewarding flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Webster County?
According to Orbitz data from 2020, you'll want to jump on a plane on a Monday to score cheap flights to Webster County. Next cheapest day? Tuesday. Saturday costs the most. So, depart early in the week if you want to score a bargain fare without paying premium prices.
What is the cheapest month to fly to Webster County?
We won't keep you in suspense — according to Orbitz data, August is generally the cheapest month to fly. Ideal for those who want to sneak in a weekend getaway or just an escape from it all before the weather changes. The least affordable time to fly is the height of summer, with ticket prices peaking in June.
Which airlines allow free cancellation?
If you're concerned your travel plans could change, Orbitz can help you lock in a flexible ticket. All you need to do is click on "Filter by flexible change policies" when searching for your flights. We'll show you all the airlines that offer free cancellation and no change fees — along with our famous low prices.
What do I need for the flight to Webster County?
Flying doesn't have to be a drag. In fact it can be fun with a little pre-planning! Make your journey a hassle-free one with the following helpful tips:

  • Before you step foot on the plane, you'll need to present some type of government-issued ID, like your passport. You'll also need your boarding pass. If you're traveling with kids, check with your airline about which documents they may need.
  • Make time fly by even quicker on your short hop by packing the right gear. Think a water bottle, snacks and entertainment. If you'd like your journey to Webster County to go nice and quietly, squeeze some noise-canceling headphones or earplugs into your bag too.
  • No matter the weather outside (or how long the flight), plane cabins can get a bit chilly. Take a sweater on board to keep yourself warm and cozy.

How do I get cheap first-class/business deals to Webster County?
Experienced travelers have honed the art of finding business or first-class airfares to Webster County without the astronomical price tag. Be like them with these useful hints:

  • Be more flexible with your travel dates and hold out for big sales on business or first-class airfares.
  • Find a low-cost airline that has seats in business class. They often come with more space and a glass of bubbly — but at a more affordable price.
  • Bid for an upgrade in online auctions (if available) or upgrade with your frequent flyer points.

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.