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

View $69 flight on Mon, Dec 1, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Owensboro, KY (OWB-Owensboro-Daviess County Regional)

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, Nov 24 - Wed, Nov 26
ORD
Chicago
OWB
Owensboro
$138 Roundtrip, found 2 hours ago
$138
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Mon, Nov 24 from Chicago to Owensboro, returning Wed, Nov 26, priced at $138 found 2 hours ago
Contour Airlines
Thu, Dec 4 - Sun, Dec 7
ORD
Chicago
OWB
Owensboro
$148 Roundtrip, found 3 hours ago
$148
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Thu, Dec 4 from Chicago to Owensboro, returning Sun, Dec 7, priced at $148 found 3 hours ago
Contour Airlines
Thu, Nov 27 - Sun, Nov 30
ORD
Chicago
OWB
Owensboro
$158 Roundtrip, found 14 hours ago
$158
Roundtrip
found 14 hours ago
Select Contour Airlines flight, departing Thu, Nov 27 from Chicago to Owensboro, returning Sun, Nov 30, priced at $158 found 14 hours ago
Contour Airlines
Mon, Nov 17 - Thu, Nov 27
ORD
Chicago
OWB
Owensboro
$168 Roundtrip, found 15 hours ago
$168
Roundtrip
found 15 hours ago
Select Contour Airlines flight, departing Mon, Nov 17 from Chicago to Owensboro, returning Thu, Nov 27, priced at $168 found 15 hours ago
Contour Airlines
Mon, Nov 24 - Wed, Nov 26
ORD
Chicago
OWB
Owensboro
$173 Roundtrip, found 2 hours ago
$173
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Mon, Nov 24 from Chicago to Owensboro, returning Wed, Nov 26, priced at $173 found 2 hours ago
Contour Airlines
Thu, Nov 6 - Sun, Nov 9
ORD
Chicago
OWB
Owensboro
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Thu, Nov 6 from Chicago to Owensboro, returning Sun, Nov 9, priced at $178 found 2 hours ago
Contour Airlines
Sat, Nov 8 - Sat, Nov 15
ORD
Chicago
OWB
Owensboro
$183 Roundtrip, found 2 hours ago
$183
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Sat, Nov 8 from Chicago to Owensboro, returning Sat, Nov 15, priced at $183 found 2 hours ago
Contour Airlines
Wed, Nov 26 - Sun, Nov 30
ORD
Chicago
OWB
Owensboro
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Wed, Nov 26 from Chicago to Owensboro, returning Sun, Nov 30, priced at $193 found 2 days ago
Contour Airlines
Tue, Dec 9 - Fri, Dec 12
ORD
Chicago
OWB
Owensboro
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Tue, Dec 9 from Chicago to Owensboro, returning Fri, Dec 12, priced at $203 found 1 day ago
Contour Airlines
Sat, Nov 8 - Tue, Nov 11
ORD
Chicago
OWB
Owensboro
$209 Roundtrip, found 2 hours ago
$209
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Sat, Nov 8 from Chicago to Owensboro, returning Tue, Nov 11, priced at $209 found 2 hours ago

Find the cheapest month to fly from Chicago (ORD) to Owensboro (OWB)

November is typically the cheapest month to fly

From $98 - $178 per traveler.

Alternative airports near Owensboro

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Evansville Regional EVV. Average driving time to city center is 54 minutes. Flights from $429
EVV
Evansville Regional
Average driving time to city center54 min
Flights from $429
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
Average flight time
1 hour 30 mins

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 November. 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?
Grab a cheap one-way flight from $69 or cheap return flight from $138 from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
The cheapest month to fly from ORD to OWB is November, when there's less demand. Off-peak months are usually when you'll find lower airfares between these airports.
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 O'Hare Intl. Airport (ORD) to Owensboro-Daviess County Regional Airport (OWB)?
To find the cheapest airline that'll fly you from ORD to OWB, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the most affordable options first.
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.