$98 Cheap flights to Webster County

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Cheap flights to Webster County from $98 One Way, $196 Round Trip

$196 return flights and $98 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, Feb 27 - Wed, Mar 3
ORD
Chicago
OWB
Owensboro
$196 Roundtrip, found 6 hours ago
$196
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Feb 27 from Chicago to Owensboro, returning Wed, Mar 3, priced at $196 found 6 hours ago
Sat, Feb 27 - Wed, Mar 3
ORD
Chicago
OWB
Owensboro
$236 Roundtrip, found 6 hours ago
$236
Roundtrip
found 6 hours ago
Select United flight, departing Sat, Feb 27 from Chicago to Owensboro, returning Wed, Mar 3, priced at $236 found 6 hours ago
Mon, May 3 - Sat, May 8
ORD
Chicago
OWB
Owensboro
$347 Roundtrip, found 6 days ago
$347
Roundtrip
found 6 days ago
Select United flight, departing Mon, May 3 from Chicago to Owensboro, returning Sat, May 8, priced at $347 found 6 days ago
Mon, Dec 28 - Thu, Dec 31
CLE
Cleveland
EVV
Evansville
$397 Roundtrip, found 6 days ago
$397
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Dec 28 from Cleveland to Evansville, returning Thu, Dec 31, priced at $397 found 6 days ago
Fri, Nov 27 - Mon, Nov 30
CMH
Columbus
EVV
Evansville
$417 Roundtrip, found 3 hours ago
$417
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Nov 27 from Columbus to Evansville, returning Mon, Nov 30, priced at $417 found 3 hours ago
Fri, Oct 23 - Sat, Oct 24
ORD
Chicago
EVV
Evansville
$432 Roundtrip, found 1 day ago
$432
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 23 from Chicago to Evansville, returning Sat, Oct 24, priced at $432 found 1 day ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
PIEEvansvilleOctober 25 to October 29$236
ORDEvansvilleOctober 23 to October 24$432
IADOwensboroOctober 25 to October 28$593
SEAEvansvilleOctober 25 to October 31$627
COSEvansvilleOctober 25 to October 25$956
IADEvansvilleOctober 25 to October 28$986
*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
$85 nightly
The price is $97 total per night from Oct 21 to Oct 22
$97 total
Oct 21 - Oct 22
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
$71 nightly
The price is $84 total per night from Oct 21 to Oct 22
$84 total
Oct 21 - Oct 22
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! (934 reviews)
"Staff was friendly and helpful. The pool was warm but one of the negative sides was the pool ladder was slippery because it didn't have anything on the metal. The hot tub didn't work. We stayed for a few days and I was really glad it has breakfast and coffee."

Reviewed on Oct 19, 2026

Opens in a new windowWingate by Wyndham Owensboro
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 Oct 25 to Oct 26
$119 total
Oct 25 - Oct 26
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 ...
8.8/10 Excellent! (614 reviews)
"great place."

Reviewed on Oct 20, 2026

Opens in a new windowFairfield Inn by Marriott Owensboro
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Hampton Inn Owensboro South

Hampton Inn Owensboro South

2.5 out of 5
615 Salem Drive Owensboro KY
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $120 total per night from Nov 8 to Nov 9
$120 total
Nov 8 - Nov 9
Total with taxes and fees
Stay at this hotel in Owensboro. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (526 reviews)
"I can not say enough about the kindness of the staff! Wow! Not just check in but throughout our staff and 90% that we passed in the hallways! Incredible people! Hotel a little noisy first thing but nothing that would make me think twice - just different schedules. I would definitely recommend! Pool ..."

Reviewed on Oct 11, 2026

Opens in a new windowHampton Inn Owensboro South
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

Save more on flights to Webster County while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Webster County

Now it is easier than ever to find a discount Webster County flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Webster County

We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Webster County flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Webster County a breeze.

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 $196 and $986. But it was jet-setters beginning their trip from Chicago (ORD) who bagged the best bargains. One-way tickets to Webster County started at a low $98.
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.