$69 Cheap Flights from Chicago (ORD) to Owensboro (OWB)

View $69 flight on Thu, May 22, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Owensboro (ORD-OWB)

Prices were available within the past 7 days and start at $69 for one-way flights and $138 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Contour Airlines
Mon, May 19 - Thu, May 22
ORD
Chicago
OWB
Owensboro
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Mon, May 19 from Chicago to Owensboro, returning Thu, May 22, priced at $138 found 1 hour ago
Contour Airlines
Mon, May 19 - Thu, May 22
ORD
Chicago
OWB
Owensboro
$148 Roundtrip, found 1 hour ago
$148
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Mon, May 19 from Chicago to Owensboro, returning Thu, May 22, priced at $148 found 1 hour ago
Contour Airlines
Sat, May 10 - Mon, May 12
ORD
Chicago
OWB
Owensboro
$158 Roundtrip, just found
$158
Roundtrip
just found
Select Contour Airlines flight, departing Sat, May 10 from Chicago to Owensboro, returning Mon, May 12, priced at $158 just found
Contour Airlines
Sat, May 10 - Mon, May 12
ORD
Chicago
OWB
Owensboro
$168 Roundtrip, just found
$168
Roundtrip
just found
Select Contour Airlines flight, departing Sat, May 10 from Chicago to Owensboro, returning Mon, May 12, priced at $168 just found
Contour Airlines
Fri, Jun 27 - Sun, Jul 13
ORD
Chicago
OWB
Owensboro
$178 Roundtrip, found 16 hours ago
$178
Roundtrip
found 16 hours ago
Select Contour Airlines flight, departing Fri, Jun 27 from Chicago to Owensboro, returning Sun, Jul 13, priced at $178 found 16 hours ago
Contour Airlines
Fri, May 23 - Mon, May 26
ORD
Chicago
OWB
Owensboro
$188 Roundtrip, found 7 hours ago
$188
Roundtrip
found 7 hours ago
Select Contour Airlines flight, departing Fri, May 23 from Chicago to Owensboro, returning Mon, May 26, priced at $188 found 7 hours ago
Contour Airlines
Tue, May 6 - Fri, May 9
ORD
Chicago
OWB
Owensboro
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Tue, May 6 from Chicago to Owensboro, returning Fri, May 9, priced at $198 found 1 day ago
Contour Airlines
Tue, May 13 - Sat, May 31
ORD
Chicago
OWB
Owensboro
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Tue, May 13 from Chicago to Owensboro, returning Sat, May 31, priced at $209 found 2 days ago
Contour Airlines
Fri, May 2 - Mon, May 5
ORD
Chicago
OWB
Owensboro
$218 Roundtrip, found 6 hours ago
$218
Roundtrip
found 6 hours ago
Select Contour Airlines flight, departing Fri, May 2 from Chicago to Owensboro, returning Mon, May 5, priced at $218 found 6 hours ago
Contour Airlines
Mon, May 12 - Sat, May 31
ORD
Chicago
OWB
Owensboro
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Mon, May 12 from Chicago to Owensboro, returning Sat, May 31, priced at $228 found 2 days ago
Contour Airlines
Tue, Apr 29 - Thu, May 1
ORD
Chicago
OWB
Owensboro
$249 Roundtrip, found 10 hours ago
$249
Roundtrip
found 10 hours ago
Select Contour Airlines flight, departing Tue, Apr 29 from Chicago to Owensboro, returning Thu, May 1, priced at $249 found 10 hours ago
Contour Airlines
Tue, Apr 29 - Wed, Apr 30
ORD
Chicago
OWB
Owensboro
$279 Roundtrip, found 3 hours ago
$279
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Tue, Apr 29 from Chicago to Owensboro, returning Wed, Apr 30, priced at $279 found 3 hours ago
Flights from Chicago (ORD) to Owensboro (OWB)
Origin airport
O'Hare Intl.
Destination airport
Owensboro-Daviess County Regional
Airlines serving
Contour Airlines
Roundtrip price
$132
Distance
294 mi

Chicago to Owensboro Flights

The cheapest times to fly from Chicago to Owensboro

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Owensboro are during the month of May. You can find some of the cheapest flights from Chicago to Owensboro with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Owensboro

Sunday is one of the best days to book for cheap flights from Chicago to Owensboro: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Owensboro

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Owensboro in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Owensboro flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Owensboro airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB) cost?
You can find affordable return tickets from O’Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB) starting from $138. Grab a seat and take off on your trip. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Contour Airlines flight leaving ORD on May 17 2025 and touching down at OWB. The price was last updated on April 24 2025 and has not changed since.
What is the cheapest month to fly from ORD to OWB?
The cheapest flights from ORD to OWB are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
You can travel nonstop from O’Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB) on a Contour Aviation flight.
What is the cheapest airline that flies from ORD to OWB?
With tickets starting at $69 for a one-way flight from ORD to OWB, Contour Airlines is currently the cheapest airline flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on July 16 2025. Prices were last updated on April 24 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
On average, there’s only 1 nonstop flight taking off from O’Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB) every day. If this doesn’t work with your itinerary, consider flights with layovers. Just customize your search on Expedia to include one stop or more to discover the next best option.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
Flights between ORD and OWB are their busiest at 10 AM. For a more relaxed experience and potentially cheaper fares, look for a departure outside the usual busy windows.
What day of the week has the most flights from ORD to OWB?
Jet off on a Friday if you’re searching for the largest selection of flights from O’Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
O’Hare Intl. Airport (ORD)’s earliest flight to Owensboro-Daviess County Regional Airport (OWB) departs at approximately 10:25AM UTC-6. With a flight time of 1h 30m, you’ll land at around 11:55AM UTC-6.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
Typically, it takes 1 hour and 30 minutes to cover the 300 mi from ORD to OWB.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
Book a flight from O’Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB) that takes off before 3 PM to reduce the risk of delays and cancellations. Later departures have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Owensboro from O'Hare Intl. Airport (ORD)?
You can arrive at Evansville Regional Airport (EVV) or Owensboro-Daviess County Regional Airport (OWB) when you travel to Owensboro on a direct flight from O’Hare Intl. Airport (ORD).
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB) last-minute?
Booking your plane ticket from ORD to OWB shortly before your getaway is generally more expensive. However, if there’s some wiggle room with your departure dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book an ORD to OWB flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to OWB flight and hotel package with Expedia could result in significant savings. What’s more, managing everything in one place will take the hassle out of planning your trip. Simply secure your flights and select from our wide range of hotels, then customize your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
Usually, it’s possible to reschedule or cancel your ORD to OWB flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline’s policies in your itinerary to see what changes are allowed and whether any costs are involved. You’ll also find further details on our Customer Service portal.

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*Available to One Key members.