$52 Cheap flights to Webster County

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Cheap flights to Webster County from $52 One Way, $128 Round Trip

$128 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.

Sat, Oct 3 - Wed, Oct 7
MCO
Orlando
EVV
Evansville
$128 Roundtrip, found 5 hours ago
$128
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Oct 3 from Orlando to Evansville, returning Wed, Oct 7, priced at $128 found 5 hours ago
Sat, Oct 3 - Sat, Oct 10
ORD
Chicago
OWB
Owensboro
$178 Roundtrip, found 14 hours ago
$178
Roundtrip
found 14 hours ago
Select Contour Airlines flight, departing Sat, Oct 3 from Chicago to Owensboro, returning Sat, Oct 10, priced at $178 found 14 hours ago
Thu, Sep 17 - Mon, Sep 21
CLT
Charlotte
OWB
Owensboro
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Thu, Sep 17 from Charlotte to Owensboro, returning Mon, Sep 21, priced at $188 found 2 days ago
Thu, Oct 15 - Tue, Oct 20
AUS
Austin
OWB
Owensboro
$342 Roundtrip, found 5 days ago
$342
Roundtrip
found 5 days ago
Select United flight, departing Thu, Oct 15 from Austin to Owensboro, returning Tue, Oct 20, priced at $342 found 5 days ago
Sat, Nov 21 - Tue, Nov 24
AUS
Austin
EVV
Evansville
$441 Roundtrip, found 4 hours ago
$441
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, Nov 21 from Austin to Evansville, returning Tue, Nov 24, priced at $441 found 4 hours ago
Wed, Sep 9 - Wed, Sep 16
ORD
Chicago
EVV
Evansville
$479 Roundtrip, found 4 hours ago
$479
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Sep 9 from Chicago to Evansville, returning Wed, Sep 16, priced at $479 found 4 hours ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
ORDOwensboroSeptember 12 to September 13$181
PIEEvansvilleSeptember 13 to September 17$208
ORDEvansvilleSeptember 12 to September 13$511
COSEvansvilleSeptember 11 to September 12$579
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Webster County Accommodation Deals

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
$77 nightly
The price is $87 total per night from Sep 6 to Sep 7
$87 total
Sep 6 - Sep 7
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 ...
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
$75 nightly
The price is $88 total per night from Sep 20 to Sep 21
$88 total
Sep 20 - Sep 21
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 ...
Opens in a new windowWingate by Wyndham Owensboro
Baymont by Wyndham Madisonville

Baymont by Wyndham Madisonville

2.5 out of 5
1891 Lantaff Blvd Madisonville KY
$98 nightly
The price is $109 total per night from Sep 13 to Sep 14
$109 total
Sep 13 - Sep 14
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 and the clean rooms in our reviews. ...
Opens in a new windowBaymont by Wyndham Madisonville
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Fairfield Inn by Marriott Owensboro

Fairfield Inn by Marriott Owensboro

3 out of 5
800 Salem Dr Owensboro KY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $119 total per night from Sep 7 to Sep 8
$119 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Owensboro. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (596 reviews)
"Great location close to everything! Friendly hotel on-site staff. We will book again for next trip to Owensboro, KY."

Reviewed on Aug 27, 2026

Opens in a new windowFairfield Inn by Marriott Owensboro
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

Frequently asked questions

Which airlines fly to Webster County?
You're spoiled for choice with 12 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 $128 and $579. But it was jet-setters beginning their trip from Orlando (MCO) 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.