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$51+ Cheap flights from Illinois to Owensboro (OWB)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — OWB
Jan 26 — Feb 21
Mon 1/26
Mon 2/2
1 adult, Economy
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Cheap flight deals from Illinois to Owensboro

Cheapest flights from Illinois to Owensboro
Explore the most affordable flight options available from Illinois to Owensboro. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 27, 2025.

This Booking.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:55 amORD - OWB
Nonstop1h 30mContour
Wed 1/71:55 pmOWB - ORD
Nonstop1h 35mContour
Deal found 12/26$182
This Booking.com deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:30 pmORD - OWB
Nonstop1h 30mContour
Wed 12/313:10 pmOWB - ORD
Nonstop1h 35mContour
Deal found 12/24$207
This Booking.com deal was found by Cheapflights users on 12/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2810:55 amORD - OWB
Nonstop1h 30mContour
Fri 1/23:10 pmOWB - ORD
Nonstop1h 35mContour
Deal found 12/26$242
This Booking.com deal was found by Cheapflights users on 12/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/285:30 pmORD - OWB
Nonstop1h 30mContour
Tue 12/301:55 pmOWB - ORD
Nonstop1h 35mContour
Deal found 12/24$257
This Contour deal was found by Cheapflights users on 12/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/309:40 amORD - OWB
Nonstop1h 30mContour
Wed 12/318:40 amOWB - ORD
Nonstop1h 35mContour
Deal found 12/25$268

Find flight deals from Illinois to Owensboro

Keep the following information in mind while searching for Illinois to Owensboro flight deals. Data was last updated December 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$105
(Mytrip)

One-way from

$51
(Flightnetwork)

Popular in

June

Cheapest in

January

Good round-trip deal

$109 or less
Provider with most accurate pricing for Chicago (CHI)-Owensboro Daviess County flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Owensboro Daviess County flights.
Search Deals
From Illinois to Owensboro Daviess County
Search Deals
One-way flight from Illinois to Owensboro Daviess County
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Price to beat on a round-trip flight from Illinois to Owensboro Daviess County.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Owensboro that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 27, 2025.
Use the filters below to find and compare flights from Illinois to Owensboro that are best for you.

Fly from

Illinois

Fly to

Owensboro

Route

Depart

Return

Price

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Fri 1/9

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Tue 1/13

1:55 pm-3:30 pm

Nonstop1h 35m

$105

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 3/12

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Sat 3/21

1:55 pm-3:30 pm

Nonstop1h 35m

$107

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Mon 2/23

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Wed 2/25

1:55 pm-3:30 pm

Nonstop1h 35m

$107

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Sat 1/24

9:40 am-11:10 am

Nonstop1h 30m

Owensboro Daviess County

Sun 1/25

8:40 am-10:15 am

Nonstop1h 35m

$119

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 2/12

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Mon 2/16

3:10 pm-4:45 pm

Nonstop1h 35m

$119

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Sat 1/10

9:40 am-11:10 am

Nonstop1h 30m

Owensboro Daviess County

Wed 1/14

1:55 pm-3:30 pm

Nonstop1h 35m

$119

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Wed 12/31

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Wed 1/7

1:55 pm-3:30 pm

Nonstop1h 35m

$182

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Mon 1/26

10:55 am-12:25 pm

Nonstop1h 30m

$51

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 1/8

5:30 pm-7:00 pm

Nonstop1h 30m

$53

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Fri 1/2

5:30 pm-7:00 pm

Nonstop1h 30m

$78

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Best time to book a flight from Illinois to Owensboro

Have a flexible travel schedule? Discover the best time to fly to Owensboro from Illinois with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Owensboro

What is the cheapest month to book a flight from Illinois to Owensboro?

Currently, December is the cheapest month in which you can book a flight from Illinois to Owensboro (average of $100). Flying from Illinois to Owensboro in July is currently the most expensive (average of $234). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IL to OWB?

Find hourly flight availability from Illinois to Owensboro. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 27, 2025.

When flying from Illinois to Owensboro, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Owensboro. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Owensboro from Illinois?

    Most people fly into Owensboro Daviess County (OWB) if they book a flight to Owensboro from Illinois. Daviess County is conveniently located just 3.6 mi from Owensboro’s city center.

  • How long is the flight from Illinois to Owensboro?

    A quick flight from Illinois to Owensboro can take about 1h 30m. Contour provides one of the quickest options available for as low as $105. The distance from Illinois to Owensboro is about 295 mi. Generally, flights for this route are nonstop.

  • Can I find deals for flights from Illinois to Owensboro that include hotel bookings?

    Yes. In addition to deals on Illinois to Owensboro flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Owensboro?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Owensboro.

  • Can I find deals for business class flights from Illinois to Owensboro?

    Yes. Cheapflights offers flight deals from Illinois to Owensboro by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Illinois to Owensboro?

    Currently, December is the cheapest month in which you can book a flight from Illinois to Owensboro (average of $100). Flying from Illinois to Owensboro in July is currently the most expensive (average of $234). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Illinois to Owensboro

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Illinois to Owensboro

Discover the top airline that operate flights from Illinois to Owensboro. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$126Average$148FlexibilityNo cancel feeOn-timeN/A

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