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Owensboro

$78+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OWB
Jun 28 — Jul 51
Sun 6/28
Sun 7/5
1 adult, Economy
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Cheap 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 May 29, 2026.

This Mytrip deal was found by Cheapflights users on 5/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1111:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Sun 6/149:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/26$147
This Mytrip deal was found by Cheapflights users on 5/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1011:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Sun 6/149:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/26$162
This Mytrip deal was found by Cheapflights users on 5/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/911:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Sat 6/139:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/25$164
This Contour deal was found by Cheapflights users on 5/28. 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 8/2511:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Wed 8/269:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/28$178
This Contour deal was found by Cheapflights users on 5/27. 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.
Wed 6/1711:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Fri 6/199:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/27$304
This Booking.com deal was found by Cheapflights users on 5/27. 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.
Sat 6/611:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Sun 6/79:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/27$331
This Booking.com deal was found by Cheapflights users on 5/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/511:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Sun 6/79:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/25$333
This deal was found by Cheapflights users on 5/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Tue 6/24:25 pm
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/26$368
This deal was found by Cheapflights users on 5/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/111:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Thu 6/49:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 5/27$388
This Mytrip deal was found by Cheapflights users on 5/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:19 pm
ORD
-
OWB
2 stops22h 31m
Multiple Airlines
Sun 6/149:00 am
OWB
-
ORD
Nonstop1h 40m
Multiple Airlines
Deal found 5/26$430

Find 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 May 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$147
(Mytrip)

One-way from

$78
(Booking.com)

Popular in

April

Cheapest in

January

Average price

$233

Good round-trip deal

$203 or less

Good one-way deal

$100 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 Chicago (CHI) to Owensboro Daviess County
Search Deals
One-way flight from Chicago (CHI) to Owensboro Daviess County
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($39 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Owensboro Daviess County.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Owensboro Daviess County.
Search Deals

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 May 29, 2026.
Use the filters below to find and compare flights from Chicago to Owensboro that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 6/11

11:20 am-12:55 pm

Nonstop1h 35m

Owensboro Daviess County

Sun 6/14

9:00 am-10:40 am

Nonstop1h 40m

$147

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Tue 8/25

11:20 am-12:55 pm

Nonstop1h 35m

Owensboro Daviess County

Wed 8/26

9:00 am-10:40 am

Nonstop1h 40m

$178

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Wed 6/17

11:20 am-12:55 pm

Nonstop1h 35m

Owensboro Daviess County

Fri 6/19

9:00 am-10:40 am

Nonstop1h 40m

$304

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Fri 6/12

11:20 am-12:55 pm

Nonstop1h 35m

Owensboro Daviess County

Tue 6/16

4:25 pm-6:05 pm

Nonstop1h 40m

$331

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Mon 6/1

11:20 am-12:55 pm

Nonstop1h 35m

Owensboro Daviess County

Thu 6/4

9:00 am-10:40 am

Nonstop1h 40m

$388

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 6/11

11:20 am-12:55 pm

Nonstop1h 35m

Owensboro Daviess County

Sun 6/14

2:15 pm-8:03 am

3 stops41h 48m

$430

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Tue 6/9

12:48 pm-6:50 pm

3 stops30h 02m

Owensboro Daviess County

Sat 6/13

9:00 am-10:40 am

Nonstop1h 40m

$497
Cheapest one-way
Quickest one-way

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Fri 6/26

11:20 am-12:55 pm

Nonstop1h 35m

$78

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Sat 6/27

11:20 am-12:55 pm

Nonstop1h 35m

$78

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Tue 6/9

11:20 am-12:55 pm

Nonstop1h 35m

$89

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

Compare providers for flights from Chicago to Owensboro

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Owensboro in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Owensboro flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Owensboro flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Owensboro flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Owensboro flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Owensboro flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 month to book a flight from Chicago to Owensboro?

Currently, July is the cheapest month in which you can book a flight from Chicago to Owensboro (average of $69). Flying from Chicago to Owensboro in May is currently the most expensive (average of $170). 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 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 May 29, 2026.

When flying from Chicago 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.

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 May 29, 2026.

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

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 May 29, 2026.
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
7.7
Good
41 reviews

Crew

8.0

Comfort

7.4

Food

6.9

Entertainment

6.2

Overall

7.7

Boarding

7.7

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo
Contour
7.7
Good
41 reviews
Contour
7.7
Good
41 reviews

Crew

8.0

Comfort

7.4

Food

6.9

Entertainment

6.2

Overall

7.7

Boarding

7.7

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo

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 $147, Contour can have you in Owensboro from Chicago in 1h 35m. 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 $104, was found to be the cheapest airline from Chicago to Owensboro.. Contour is priced at 40% 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 $167, our data shows the cheapest flight currently is $61. When looking at the most popular route, (Chicago O'Hare Intl - Owensboro Daviess County), you can expect to pay $178 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.

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

    Currently, July is the cheapest month in which you can book a flight from Chicago to Owensboro (average of $69). Flying from Chicago to Owensboro in May is currently the most expensive (average of $170). 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

Browse thousands of different options on Cheapflights for your next trip

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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 May 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$104Average$148FlexibilityNo cancel feeOn-timeN/A

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