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

View $69 flight on Sat, Nov 1, 2025Opens in a new window

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

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Cheap Flights from Owensboro to Chicago (OWB-ORD)

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, Sep 22 - Thu, Sep 25
OWB
Owensboro
ORD
Chicago
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Mon, Sep 22 from Owensboro to Chicago, returning Thu, Sep 25, priced at $138 found 1 hour ago
Contour Airlines
Mon, Sep 22 - Fri, Sep 26
OWB
Owensboro
ORD
Chicago
$148 Roundtrip, found 1 hour ago
$148
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Mon, Sep 22 from Owensboro to Chicago, returning Fri, Sep 26, priced at $148 found 1 hour ago
Contour Airlines
Thu, Aug 21 - Sun, Aug 24
OWB
Owensboro
ORD
Chicago
$158 Roundtrip, just found
$158
Roundtrip
just found
Select Contour Airlines flight, departing Thu, Aug 21 from Owensboro to Chicago, returning Sun, Aug 24, priced at $158 just found
Contour Airlines
Fri, Aug 29 - Mon, Sep 1
OWB
Owensboro
ORD
Chicago
$168 Roundtrip, just found
$168
Roundtrip
just found
Select Contour Airlines flight, departing Fri, Aug 29 from Owensboro to Chicago, returning Mon, Sep 1, priced at $168 just found
Contour Airlines
Thu, Aug 14 - Wed, Aug 20
OWB
Owensboro
ORD
Chicago
$188 Roundtrip, just found
$188
Roundtrip
just found
Select Contour Airlines flight, departing Thu, Aug 14 from Owensboro to Chicago, returning Wed, Aug 20, priced at $188 just found
Contour Airlines
Thu, Aug 14 - Wed, Aug 20
OWB
Owensboro
ORD
Chicago
$198 Roundtrip, just found
$198
Roundtrip
just found
Select Contour Airlines flight, departing Thu, Aug 14 from Owensboro to Chicago, returning Wed, Aug 20, priced at $198 just found
Contour Airlines
Sun, Aug 3 - Thu, Aug 21
OWB
Owensboro
ORD
Chicago
$209 Roundtrip, found 16 hours ago
$209
Roundtrip
found 16 hours ago
Select Contour Airlines flight, departing Sun, Aug 3 from Owensboro to Chicago, returning Thu, Aug 21, priced at $209 found 16 hours ago
Contour Airlines
Sat, Aug 9 - Tue, Aug 12
OWB
Owensboro
ORD
Chicago
$218 Roundtrip, found 3 hours ago
$218
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Sat, Aug 9 from Owensboro to Chicago, returning Tue, Aug 12, priced at $218 found 3 hours ago
Contour Airlines
Wed, Aug 6 - Sun, Aug 10
OWB
Owensboro
ORD
Chicago
$249 Roundtrip, found 2 hours ago
$249
Roundtrip
found 2 hours ago
Select Contour Airlines flight, departing Wed, Aug 6 from Owensboro to Chicago, returning Sun, Aug 10, priced at $249 found 2 hours ago

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

October is typically the cheapest month to fly

From $98 - $158 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $148
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $148
Flights from Owensboro (OWB) to Chicago (ORD)
Origin airport
Owensboro-Daviess County Regional
Destination airport
O'Hare Intl.
Airlines serving
Contour Airlines
Roundtrip price
$132
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 September. 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 $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 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?
Find cheap return fares from Owensboro-Daviess County Regional Airport (OWB) to O'Hare Intl. Airport (ORD) starting at $133. Reserve your seat and get ready to go. 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 OWB on August 19 2025 and touching down at ORD. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from OWB to ORD?
The cheapest flights from OWB to ORD 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 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 OWB to ORD?
Fly from OWB to ORD with Contour Airlines. This carrier currently has the cheapest one-way ticket for this route, starting at $69. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from OWB on September 22 2025. Prices were last updated on July 23 2025 and have not changed since.
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.

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