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

View $69 flight on Sat, Jun 7, 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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Find available prices by choosing your travel dates.

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
Thu, May 15 - Wed, May 21
OWB
Owensboro
ORD
Chicago
$138 Roundtrip, found 4 hours ago
$138
Roundtrip
found 4 hours ago
Select Contour Airlines flight, departing Thu, May 15 from Owensboro to Chicago, returning Wed, May 21, priced at $138 found 4 hours ago
Contour Airlines
Fri, Aug 15 - Mon, Aug 18
OWB
Owensboro
ORD
Chicago
$148 Roundtrip, found 1 hour ago
$148
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Fri, Aug 15 from Owensboro to Chicago, returning Mon, Aug 18, priced at $148 found 1 hour ago
Contour Airlines
Fri, Aug 15 - Mon, Aug 18
OWB
Owensboro
ORD
Chicago
$158 Roundtrip, found 1 hour ago
$158
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Fri, Aug 15 from Owensboro to Chicago, returning Mon, Aug 18, priced at $158 found 1 hour ago
Contour Airlines
Fri, Aug 15 - Mon, Aug 18
OWB
Owensboro
ORD
Chicago
$168 Roundtrip, found 1 hour ago
$168
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Fri, Aug 15 from Owensboro to Chicago, returning Mon, Aug 18, priced at $168 found 1 hour ago
Contour Airlines
Fri, Aug 15 - Mon, Aug 18
OWB
Owensboro
ORD
Chicago
$178 Roundtrip, found 1 hour ago
$178
Roundtrip
found 1 hour ago
Select Contour Airlines flight, departing Fri, Aug 15 from Owensboro to Chicago, returning Mon, Aug 18, priced at $178 found 1 hour ago
Contour Airlines
Thu, May 1 - Thu, May 8
OWB
Owensboro
ORD
Chicago
$188 Roundtrip, found 3 hours ago
$188
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Thu, May 1 from Owensboro to Chicago, returning Thu, May 8, priced at $188 found 3 hours ago
Contour Airlines
Thu, May 1 - Fri, May 9
OWB
Owensboro
ORD
Chicago
$198 Roundtrip, found 3 hours ago
$198
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Thu, May 1 from Owensboro to Chicago, returning Fri, May 9, priced at $198 found 3 hours ago
Contour Airlines
Sat, May 31 - Tue, Jun 3
OWB
Owensboro
ORD
Chicago
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Sat, May 31 from Owensboro to Chicago, returning Tue, Jun 3, priced at $209 found 2 days ago
Contour Airlines
Fri, May 2 - Tue, May 6
OWB
Owensboro
ORD
Chicago
$218 Roundtrip, found 3 hours ago
$218
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Fri, May 2 from Owensboro to Chicago, returning Tue, May 6, priced at $218 found 3 hours ago
Contour Airlines
Mon, Apr 28 - Fri, May 9
OWB
Owensboro
ORD
Chicago
$228 Roundtrip, found 3 hours ago
$228
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Mon, Apr 28 from Owensboro to Chicago, returning Fri, May 9, priced at $228 found 3 hours ago
Contour Airlines
Sat, May 31 - Tue, Jun 3
OWB
Owensboro
ORD
Chicago
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Sat, May 31 from Owensboro to Chicago, returning Tue, Jun 3, priced at $238 found 1 day ago
Contour Airlines
Mon, Apr 28 - Sat, May 3
OWB
Owensboro
ORD
Chicago
$249 Roundtrip, found 3 hours ago
$249
Roundtrip
found 3 hours ago
Select Contour Airlines flight, departing Mon, Apr 28 from Owensboro to Chicago, returning Sat, May 3, priced at $249 found 3 hours ago
Contour Airlines
Fri, May 23 - Sun, May 25
OWB
Owensboro
ORD
Chicago
$278 Roundtrip, found 2 days ago
$278
Roundtrip
found 2 days ago
Select Contour Airlines flight, departing Fri, May 23 from Owensboro to Chicago, returning Sun, May 25, priced at $278 found 2 days ago
Contour Airlines
Sat, Apr 26 - Sun, Apr 27
OWB
Owensboro
ORD
Chicago
$308 Roundtrip, found 12 hours ago
$308
Roundtrip
found 12 hours ago
Select Contour Airlines flight, departing Sat, Apr 26 from Owensboro to Chicago, returning Sun, Apr 27, priced at $308 found 12 hours ago

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 May 15 2025 and touching down at ORD. The price was last updated on April 24 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 July 14 2025. Prices were last updated on April 24 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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