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$101+ Cheap flights from Chicago (CHI) 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OWB
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$127
(Booking.com)

One-way from

$101
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$163

Good round-trip deal

$148 or less

Good one-way deal

$83 or less
From Chicago (CHI) to Owensboro Daviess County
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One-way flight from Chicago (CHI) to Owensboro Daviess County
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Highest demand for flights based on searches. 15% potential increase in price ($32 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 July 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 July 31, 2025.

This Booking.com deal was found by Cheapflights users on 7/30. 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.
Tue 11/1110:10 amORD - OWB
Nonstop1h 30mContour
Sat 11/157:15 amOWB - ORD
Nonstop1h 35mContour
Deal found 7/30$127

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 July 31, 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 10/2

4:30 pm-6:00 pm

Nonstop1h 30m

Owensboro Daviess County

Mon 10/6

7:30 am-9:05 am

Nonstop1h 35m

$138

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Mon 8/11

5:10 pm-6:40 pm

Nonstop1h 30m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 31, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 11% on flights from Chicago to Owensboro by exploring options for tickets at noon.

Weekly flight availability from Chicago to Owensboro

Explore weekly flight availability from Chicago to Owensboro. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 31, 2025.

The most flights from CHI to OWB are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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.

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

    Contour, at $127, was found to be the cheapest airline from Chicago to Owensboro.. Contour is priced at 25% 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 $152, our data shows the cheapest flight currently is $79. When looking at the most popular route, (Chicago O'Hare Intl - Owensboro Daviess County), you can expect to pay $127 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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See prices for flight routes from nearby airports that may be better suited for you.
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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$102Average$138FlexibilityNo cancel feeOn-timeN/A

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