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Owensboro

$126+ Cheap flights from Chicago (CHI) to Owensboro (OWB)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OWB
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Chicago to Owensboro

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Owensboro (OWB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$131
(Booking.com)

Popular in

December

Cheapest in

February

Average price

$131

Good round-trip deal

$137 or less

Good one-way deal

$130 or less
From Chicago (CHI) to Owensboro Daviess County
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Highest demand for flights based on searches. 16% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Owensboro Daviess County.
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Price to beat on a one-way flight from Chicago (CHI) to Owensboro Daviess County.
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Find flight deals from Chicago to Owensboro

Cheapest flights from Chicago to Owensboro
Explore the most affordable flight options available from Chicago to Owensboro. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1610:10 amORD - OWB
Nonstop1h 30mContour
Tue 9/232:00 pmOWB - ORD
Nonstop1h 35mContour
Deal found 9/15$126
This FlightHub deal was found by Cheapflights users on 9/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2010:10 amORD - OWB
Nonstop1h 30mContour
Tue 9/302:00 pmOWB - ORD
Nonstop1h 35mContour
Deal found 9/15$138
This Contour deal was found by Cheapflights users on 9/16. 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 9/3010:10 amORD - OWB
Nonstop1h 30mContour
Fri 10/38:40 amOWB - ORD
Nonstop1h 35mContour
Deal found 9/16$158
This Contour deal was found by Cheapflights users on 9/15. 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.
Sun 9/2810:10 amORD - OWB
Nonstop1h 30mContour
Wed 10/18:40 amOWB - ORD
Nonstop1h 35mContour
Deal found 9/15$183
This FlightHub deal was found by Cheapflights users on 9/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/184:30 pmORD - OWB
Nonstop1h 30mContour
Tue 9/232:00 pmOWB - ORD
Nonstop1h 35mContour
Deal found 9/15$238

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago to Owensboro that are best for you.

Fly from

Chicago

Fly to

Owensboro

Route

Depart

Return

Price

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 10/9

5:30 pm-7:00 pm

Nonstop1h 30m

Owensboro Daviess County

Mon 10/13

8:40 am-10:15 am

Nonstop1h 35m

$131

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 10/9

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Fri 10/10

8:40 am-10:15 am

Nonstop1h 35m

$133

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Wed 10/8

5:30 pm-7:00 pm

Nonstop1h 30m

Owensboro Daviess County

Fri 10/10

8:40 am-10:15 am

Nonstop1h 35m

$134

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Wed 10/15

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Wed 10/22

8:40 am-10:15 am

Nonstop1h 35m

$138

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Mon 9/29

4:30 pm-6:00 pm

Nonstop1h 30m

Owensboro Daviess County

Thu 10/2

8:40 am-10:15 am

Nonstop1h 35m

$138

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Tue 10/7

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Fri 10/10

8:40 am-10:15 am

Nonstop1h 35m

$143

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Fri 10/17

5:30 pm-7:00 pm

Nonstop1h 30m

Owensboro Daviess County

Sun 10/26

3:00 pm-4:35 pm

Nonstop1h 35m

$158

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Tue 9/30

10:10 am-11:40 am

Nonstop1h 30m

Owensboro Daviess County

Fri 10/3

8:40 am-10:15 am

Nonstop1h 35m

$158

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Sun 9/28

10:10 am-11:40 am

Nonstop1h 30m

Owensboro Daviess County

Wed 10/1

8:40 am-10:15 am

Nonstop1h 35m

$183

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Best time to book a flight from Chicago to Owensboro

Have a flexible travel schedule? Discover the best time to fly to Owensboro from Chicago 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 Chicago to Owensboro

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

Find hourly flight availability from Chicago 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 September 17, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 3% on flights from Chicago to Owensboro by exploring options for tickets at noon.

How much does it cost to fly round-trip from Chicago to Owensboro?

Reviews of airlines servicing Owensboro

Get insights into the airlines that provide service to Owensboro. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Owensboro. Reviews last updated September 17, 2025.
Read reviews from past customers who have flown Contour from Chicago to Owensboro. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Contour
7.2
Good
36 reviews

Overall

7.2

Boarding

7.2

Crew

7.6

Comfort

7.0

Food

6.5

Entertainment

6.1

Reviews

1 / 1
2.0
Mediocre

Kavita,Aug 2025

PAH - CLT

Flight was canceled after hours of delays due to a maintenance issue. Contour offered no assistance with rebooking, finding a hotel for the night, or transportation even though the next flight was not until the next morning.
Contour
7.2
Good
36 reviews
Contour
7.2
Good
36 reviews

Overall

7.2

Boarding

7.2

Crew

7.6

Comfort

7.0

Food

6.5

Entertainment

6.1

Reviews

1 / 1
2.0
Mediocre

Kavita,Aug 2025

PAH - CLT

Flight was canceled after hours of delays due to a maintenance issue. Contour offered no assistance with rebooking, finding a hotel for the night, or transportation even though the next flight was not until the next morning.

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 Chicago?

    Located just 3.6 mi from the city center, Owensboro Daviess County is the airport most travelers will use when flying to Owensboro from Chicago. Booking flights from Chicago to Daviess County (OWB) should be relatively easy as there is 1 daily inbound flight from Chicago from 1 airline.

  • How long is the flight from Chicago to Owensboro?

    For as low as $131, Contour can have you in Owensboro from Chicago in 1h 30m. Airlines will cover a distance of 295 mi. All flights are typically nonstop.

  • What is the cheapest airline to fly from Chicago to Owensboro round-trip?

    Contour, at $106, was found to be the cheapest airline from Chicago to Owensboro.. Contour is priced at 37% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest flights from Chicago to Owensboro?

    While on average a flight from Chicago to Owensboro is generally $137, our data shows the cheapest flight currently is $51. When looking at the most popular route, (Chicago O'Hare Intl - Owensboro Daviess County), you can expect to pay $128 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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.

See more FAQs

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Alternative routes for Chicago to Owensboro

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Top airline flying from Chicago to Owensboro

Discover the top airline that operate flights from Chicago 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$106Average$141FlexibilityNo cancel feeOn-timeN/A

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