$59 Cheap Flights from Owensboro (OWB) to Chicago (ORD)

View $59 flight on Sat, Oct 4, 2025Opens in a new window

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

    notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
    deals illustration

    Book smarter

    Save up to 30% on select hotels after you book a flight*
    trophy illustration

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Today's featured flight deals from Owensboro, KY (OWB-Owensboro-Daviess County Regional) to Chicago O'Hare Intl. Airport (ORD)

Nonstop
Carry-on included
Lower price than typical

Cheap Flights from Owensboro to Chicago (OWB-ORD)

Prices were available within the past 7 days and start at $59 for one-way flights and $119 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Contour Airlines
Thu, Oct 2 - Sat, Oct 4
OWB
Owensboro
ORD
Chicago
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Thu, Oct 2 from Owensboro to Chicago, returning Sat, Oct 4, priced at $119 found 1 day ago
Contour Airlines
Wed, Oct 22 - Mon, Oct 27
OWB
Owensboro
ORD
Chicago
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Wed, Oct 22 from Owensboro to Chicago, returning Mon, Oct 27, priced at $138 found 1 hour ago
Contour Airlines
Sun, Dec 28 - Thu, Jan 1
OWB
Owensboro
ORD
Chicago
$148 Roundtrip, just found
$148
Roundtrip
just found
Select Contour Airlines flight, departing Sun, Dec 28 from Owensboro to Chicago, returning Thu, Jan 1, priced at $148 just found
Contour Airlines
Thu, Dec 18 - Mon, Dec 22
OWB
Owensboro
ORD
Chicago
$158 Roundtrip, just found
$158
Roundtrip
just found
Select Contour Airlines flight, departing Thu, Dec 18 from Owensboro to Chicago, returning Mon, Dec 22, priced at $158 just found
Contour Airlines
Sat, Nov 22 - Sun, Nov 23
OWB
Owensboro
ORD
Chicago
$168 Roundtrip, found 13 hours ago
$168
Roundtrip
found 13 hours ago
Select Contour Airlines flight, departing Sat, Nov 22 from Owensboro to Chicago, returning Sun, Nov 23, priced at $168 found 13 hours ago
Contour Airlines
Thu, Dec 18 - Mon, Dec 22
OWB
Owensboro
ORD
Chicago
$173 Roundtrip, just found
$173
Roundtrip
just found
Select Contour Airlines flight, departing Thu, Dec 18 from Owensboro to Chicago, returning Mon, Dec 22, priced at $173 just found
Contour Airlines
Sat, Nov 29 - Sat, Dec 20
OWB
Owensboro
ORD
Chicago
$178 Roundtrip, found 3 days ago
$178
Roundtrip
found 3 days ago
Select Contour Airlines flight, departing Sat, Nov 29 from Owensboro to Chicago, returning Sat, Dec 20, priced at $178 found 3 days ago
Contour Airlines
Tue, Nov 25 - Sun, Nov 30
OWB
Owensboro
ORD
Chicago
$183 Roundtrip, just found
$183
Roundtrip
just found
Select Contour Airlines flight, departing Tue, Nov 25 from Owensboro to Chicago, returning Sun, Nov 30, priced at $183 just found
Contour Airlines
Sat, Nov 22 - Wed, Nov 26
OWB
Owensboro
ORD
Chicago
$193 Roundtrip, found 13 hours ago
$193
Roundtrip
found 13 hours ago
Select Contour Airlines flight, departing Sat, Nov 22 from Owensboro to Chicago, returning Wed, Nov 26, priced at $193 found 13 hours ago
Contour Airlines
Tue, Nov 25 - Sun, Nov 30
OWB
Owensboro
ORD
Chicago
$203 Roundtrip, just found
$203
Roundtrip
just found
Select Contour Airlines flight, departing Tue, Nov 25 from Owensboro to Chicago, returning Sun, Nov 30, priced at $203 just found
Contour Airlines
Tue, Oct 7 - Fri, Oct 10
OWB
Owensboro
ORD
Chicago
$209 Roundtrip, found 3 hours ago
$209
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Tue, Oct 7 from Owensboro to Chicago, returning Fri, Oct 10, priced at $209 found 3 hours ago
Contour Airlines
Tue, Nov 25 - Sun, Nov 30
OWB
Owensboro
ORD
Chicago
$213 Roundtrip, just found
$213
Roundtrip
just found
Select Contour Airlines flight, departing Tue, Nov 25 from Owensboro to Chicago, returning Sun, Nov 30, priced at $213 just found
Contour Airlines
Fri, Oct 10 - Mon, Oct 13
OWB
Owensboro
ORD
Chicago
$223 Roundtrip, found 2 days ago
$223
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, Oct 10 from Owensboro to Chicago, returning Mon, Oct 13, priced at $223 found 2 days ago

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

November is typically the cheapest month to fly

From $98 - $178 per traveler.
Flights from Owensboro (OWB) to Chicago (ORD)
Origin airport
Owensboro-Daviess County Regional
Destination airport
O'Hare Intl.
Airlines serving
Contour Airlines
Roundtrip price
$112
Distance
294 mi
Average flight time
1 hour 35 mins

Owensboro to Chicago Flights

The cheapest times to fly from Owensboro to Chicago

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 Owensboro to Chicago are during the month of October. You can find some of the cheapest flights from Owensboro to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Owensboro to Chicago

Sunday is one of the best days to book for cheap flights from Owensboro to Chicago: 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 Owensboro to Chicago

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 Owensboro to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 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 Owensboro to Chicago 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 Owensboro to Chicago 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 Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $59 or cheap return flight from $119 from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
October is the cheapest month to fly from OWB to ORD. Traveling during an off-peak travel window is often the key to finding better fares.
Which airlines fly direct from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
When heading out of Owensboro-Daviess County Regional Airport (OWB), you can board a direct flight to O'Hare Intl. Airport (ORD) with Contour Aviation.
What is the cheapest airline that flies from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
Expedia's filter tool lets you easily compare different airlines, departure times and fares all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest OWB to ORD flight.
How many flights per day from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
On average, there is just 1 direct flight taking off from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD) per day. If this isn't convenient for you, consider flights with layovers. Simply filter your search on Expedia to include one stop or more to find the next best option.
What are the most popular departure times for flights from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
Flights between OWB and ORD are busiest at 7 AM. If you'd like a quieter trip and potentially cheaper prices, choose a departure that's outside typical rush times.
What day of the week has the most flights from OWB to ORD?
If you jet off on a Friday, you'll get the widest range of options for flights from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD).
What is the earliest flight from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
Owensboro-Daviess County Regional Airport (OWB)'s first flight to O'Hare Intl. Airport (ORD) leaves at approximately 7:15AM UTC-6. With a travel duration of 1h 35m, you'll arrive at around 8:50AM UTC-6.
How long does it take to fly from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
It takes about 1 hour and 35 minutes to travel the 300 mi from OWB to ORD.
What is the best time to fly from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) without delays, book a flight that leaves from Owensboro-Daviess County Regional Airport (OWB) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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 Chicago from Owensboro-Daviess County Regional Airport (OWB)?
O'Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Owensboro-Daviess County Regional Airport (OWB). Explore your options and find cheap fares on Expedia.
Is it cheaper to buy a plane ticket from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD) last-minute?
Holding off until right before your break to book a flight from OWB to ORD often results in higher prices. While you might find some last-minute offers, there's no guarantee. Be flexible with your itinerary for the best chance of scoring a bargain.
Is it cheaper to book an OWB to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking an OWB to ORD flight and hotel package with Expedia could result in significant savings. Better still, having everything in one place will take the hassle out of planning your trip. Just secure your flights and select from our extensive range of hotels, then tailor your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD)?
It's generally possible to reschedule or cancel your OWB to ORD flight. However, if it's been more than 24 hours since booking, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find further details on our Customer Service portal.

Explore a world of travel with Expedia

*Available to One Key members.