$76+ 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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — OWB
Sep 21 — Sep 281
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Chicago to Owensboro with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Owensboro
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to OwensboroExplore 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 August 22, 2026.
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 August 22, 2026.
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/2411:30 am -
Nonstop1h 30m
Mon 9/289:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$155
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/2211:30 am -
Nonstop1h 30m
Fri 9/259:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$159
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Fri 9/411:30 am -
Nonstop1h 30m
Mon 9/79:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$160
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/1611:30 am -
Nonstop1h 30m
Wed 9/239:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$163
This Booking.com deal was found by Cheapflights users on 8/17. 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 10/211:30 am -
Nonstop1h 30m
Mon 10/59:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$164
This Flightnetwork deal was found by Cheapflights users on 8/21. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/511:30 am -
Nonstop1h 30m
Mon 10/129:00 am -
Nonstop1h 50m
Deal found 8/21![Contour logo]()
$166
This Booking.com deal was found by Cheapflights users on 8/19. 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.
Thu 9/311:30 am -
Nonstop1h 30m
Mon 9/79:00 am -
Nonstop1h 50m
Deal found 8/19![Contour logo]()
$193
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:30 pm -
Nonstop1h 35m
Sun 11/152:25 pm -
Nonstop1h 50m
Deal found 8/18![United Airlines logo]()
$196
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Mon 9/711:30 am -
Nonstop1h 30m
Sat 9/199:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$214
This United Airlines deal was found by Cheapflights users on 8/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:30 pm -
Nonstop1h 35m
Thu 10/292:25 pm -
Nonstop1h 50m
Deal found 8/17![United Airlines logo]()
$236
Best flights from Chicago to OwensboroDiscover carefully curated flight deals from Chicago to Owensboro that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 22, 2026.
Discover carefully curated flight deals from Chicago to Owensboro that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 22, 2026.
This Mytrip deal was found by Cheapflights users on 8/18. 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 9/2411:30 am -
Nonstop1h 30m
Mon 9/289:00 am -
Nonstop1h 50m
Deal found 8/18![Contour logo]()
$160
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:30 pm -
Nonstop1h 35m
Sun 11/152:25 pm -
Nonstop1h 50m
Deal found 8/18![United Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:30 am -
Nonstop1h 30m
Wed 9/231:55 pm -
3 stops33h 04m
Deal found 8/17![Multiple Airlines logo]()
$313
This Contour deal was found by Cheapflights users on 8/20. 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.
Fri 9/411:30 am -
Nonstop1h 30m
Mon 9/79:00 am -
Nonstop1h 50m
Deal found 8/20![Contour logo]()
$178
This Booking.com deal was found by Cheapflights users on 8/19. 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.
Thu 9/311:30 am -
Nonstop1h 30m
Mon 9/79:00 am -
Nonstop1h 50m
Deal found 8/19![Contour logo]()
$193
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/269:30 pm -
Nonstop1h 35m
Thu 10/292:25 pm -
Nonstop1h 50m
Deal found 8/19![United Airlines logo]()
$236
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Mon 9/711:30 am -
Nonstop1h 30m
Sat 9/199:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$214
This Contour deal was found by Cheapflights users on 8/20. 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 9/211:30 am -
Nonstop1h 30m
Sat 9/59:00 am -
Nonstop1h 50m
Deal found 8/20![Contour logo]()
$293
Last-minute flights from Chicago to OwensboroDiscover last-minute flight deals from Chicago to Owensboro. Data last updated August 22, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Owensboro. Data last updated August 22, 2026 and is based on user searches.
This Contour deal was found by Cheapflights users on 8/20. 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 9/211:30 am -
Nonstop1h 30m
Sat 9/59:00 am -
Nonstop1h 50m
Deal found 8/20![Contour logo]()
$293
This Booking.com deal was found by Cheapflights users on 8/19. 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.
Thu 9/311:30 am -
Nonstop1h 30m
Mon 9/79:00 am -
Nonstop1h 50m
Deal found 8/19![Contour logo]()
$193
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Fri 9/411:30 am -
Nonstop1h 30m
Mon 9/79:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$160
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Mon 9/711:30 am -
Nonstop1h 30m
Sat 9/199:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$214
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/1611:30 am -
Nonstop1h 30m
Wed 9/239:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1611:30 am -
Nonstop1h 30m
Wed 9/231:55 pm -
3 stops33h 04m
Deal found 8/17![Multiple Airlines logo]()
$313
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/2211:30 am -
Nonstop1h 30m
Fri 9/259:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$159
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/2411:30 am -
Nonstop1h 30m
Mon 9/289:00 am -
Nonstop1h 50m
Deal found 8/17![Contour logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:20 am -
2 stops13h 00m
Mon 9/289:00 am -
Nonstop1h 50m
Deal found 8/17![Multiple Airlines logo]()
$272
One-way flights from Chicago to OwensboroSearch for one-way flight options from Chicago to Owensboro. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
Search for one-way flight options from Chicago to Owensboro. Find affordable one-way fares based on user searches. Data last updated August 22, 2026.
This Mytrip deal was found by Cheapflights users on 8/17. 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 9/2411:30 am -
Nonstop1h 30m
Deal found 8/17![Contour logo]()
$76
This Booking.com deal was found by Cheapflights users on 8/19. 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.
Mon 10/1211:30 am -
Nonstop1h 30m
Deal found 8/19![Contour logo]()
$77
This Booking.com deal was found by Cheapflights users on 8/17. 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.
Thu 9/1711:30 am -
Nonstop1h 30m
Deal found 8/17![Contour logo]()
$78
This CheapOair deal was found by Cheapflights users on 8/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/811:30 am -
Nonstop1h 30m
Deal found 8/17![Contour logo]()
$89
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:30 pm -
Nonstop1h 35m
Deal found 8/19![United Airlines logo]()
$98
This Booking.com deal was found by Cheapflights users on 8/19. 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.
Mon 9/2111:30 am -
Nonstop1h 30m
Deal found 8/19![Contour logo]()
$131
This Mytrip deal was found by Cheapflights users on 8/17. 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 8/2611:30 am -
Nonstop1h 30m
Deal found 8/17![Contour logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:20 am -
2 stops13h 00m
Deal found 8/17![Multiple Airlines logo]()
$175
This United Airlines deal was found by Cheapflights users on 8/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:30 pm -
Nonstop1h 35m
Deal found 8/20![United Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:50 pm -
2 stops27h 30m
Deal found 8/17![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:20 am -
2 stops13h 00m
Deal found 8/17![Multiple Airlines logo]()
$203
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 August 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $155 (Mytrip) |
One-way from | $76 (Mytrip) |
Popular in | April |
Cheapest in | January |
Average price | $164 |
Good round-trip deal | $134 or less |
Good one-way deal | $129 or less |
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 7,457,451 searches. Data last updated August 22, 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
Cheapest round-trip
Quickest round-trip
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Thu 9/24
11:30 am-1:00 pm
Nonstop1h 30m
Owensboro Daviess County
Mon 9/28
9:00 am-10:50 am
Nonstop1h 50m
$160
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Fri 9/4
11:30 am-1:00 pm
Nonstop1h 30m
Owensboro Daviess County
Mon 9/7
9:00 am-10:50 am
Nonstop1h 50m
$178
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Thu 9/3
11:30 am-1:00 pm
Nonstop1h 30m
Owensboro Daviess County
Mon 9/7
9:00 am-10:50 am
Nonstop1h 50m
$193
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Wed 11/11
9:30 pm-11:05 pm
Nonstop1h 35m
Owensboro Daviess County
Sun 11/15
2:25 pm-4:15 pm
Nonstop1h 50m
$196
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Mon 9/7
11:30 am-1:00 pm
Nonstop1h 30m
Owensboro Daviess County
Sat 9/19
9:00 am-10:50 am
Nonstop1h 50m
$214
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Mon 10/26
9:30 pm-11:05 pm
Nonstop1h 35m
Owensboro Daviess County
Thu 10/29
2:25 pm-4:15 pm
Nonstop1h 50m
$236
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Wed 9/2
11:30 am-1:00 pm
Nonstop1h 30m
Owensboro Daviess County
Sat 9/5
9:00 am-10:50 am
Nonstop1h 50m
$293
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Wed 9/16
11:30 am-1:00 pm
Nonstop1h 30m
Owensboro Daviess County
Wed 9/23
1:55 pm-10:59 pm
3 stops33h 04m
$313
Cheapest one-way
Quickest one-way
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Thu 9/24
11:30 am-1:00 pm
Nonstop1h 30m
$76
ChicagoOwensboro
ORD Chicago O'Hare Intl - OWB Owensboro Daviess County
ORDOWB
Chicago O'Hare Intl
Tue 9/22
11:30 am-1:00 pm
Nonstop1h 30m
$76
Showing 1-10 of 17 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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.
CHI-OWB
ORD-OWB
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
CHI-OWB
ORD-OWB
What is the cheapest month to book a flight from Chicago to Owensboro?
Currently, January is the cheapest month in which you can book a flight from Chicago to Owensboro (average of $118). Flying from Chicago to Owensboro in May is currently the most expensive (average of $231). 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 August 22, 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 August 22, 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).
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 August 22, 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.
Food
6.8
Overall
7.5
Crew
7.8
Comfort
7.3
Entertainment
6.1
Boarding
7.5
Reviews
1 / 2
10.0
ExcellentAnonymous,Oct 2025
CLT - PAH
Food
6.8
Overall
7.5
Crew
7.8
Comfort
7.3
Entertainment
6.1
Boarding
7.5
Reviews
1 / 2
10.0
ExcellentAnonymous,Oct 2025
CLT - PAH
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from Chicago
Owensboro flight routes
Popular flights
Alternative routes for Chicago to Owensboro
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Owensboro by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Owensboro by cabin class
Find flights from Chicago to Owensboro, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Owensboro flights
Browse other Chicago and Owensboro flight options. Last updated on August 22, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on August 22, 2026.
Other flights to Owensboro
Explore flights to Owensboro departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated August 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$104 | Average$151 | FlexibilityNo cancel fee | On-timeN/A |