ORD - OWB

$78 Find Cheap Flights from Chicago to Owensboro - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Owensboro departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$161
Typical prices: $137-$199
Contour
Tue 8/4Tue 8/11
ORD - OWB • Non-stop
Cheapest one-way
$78
Typical prices: $71-$130
Contour
Wed 8/19
ORD - OWB • Non-stop
Top airlines
Contour
Cheapest • from $161 (round-trip)
Contour
Best reviews • 7.7 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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Nonstop flights
Every day
You can fly direct with Contour. Average duration is 1h 35m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
November
Cheapest • 100% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Owensboro!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Owensboro (ORD-OWB)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Owensboro that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Owensboro

Tue, Aug 4 - Tue, Aug 11
Contour Logo
11:30 am - 1:00 pm
ORD
-
OWB
1h 30mnonstop
Contour Logo
9:00 am - 10:50 am
OWB
-
ORD
1h 50mnonstop
$161Contour
Tue, Aug 4 - Tue, Aug 11
Contour Logo
11:30 am - 1:00 pm
ORD
-
OWB
1h 30mnonstop
Contour Logo
9:00 am - 10:50 am
OWB
-
ORD
1h 50mnonstop
$162Contour
Sat, Aug 1 - Thu, Aug 6
Contour Logo
11:30 am - 1:00 pm
ORD
-
OWB
1h 30mnonstop
Contour Logo
9:00 am - 10:50 am
OWB
-
ORD
1h 50mnonstop
$165Contour
Fri, Sep 25 - Sun, Sep 27
Contour Logo
11:30 am - 1:00 pm
ORD
-
OWB
1h 30mnonstop
Contour Logo
9:00 am - 10:50 am
OWB
-
ORD
1h 50mnonstop
$166Contour
Thu, Aug 6 - Sun, Aug 9
Contour Logo
11:30 am - 1:00 pm
ORD
-
OWB
1h 30mnonstop
Contour Logo
9:00 am - 10:50 am
OWB
-
ORD
1h 50mnonstop
$178Contour
Mon, Aug 3 - Fri, Aug 7
Contour Logo
11:30 am - 1:00 pm
ORD
-
OWB
1h 30mnonstop
Contour Logo
9:00 am - 10:50 am
OWB
-
ORD
1h 50mnonstop
$298Contour
Tue, Aug 4 - Tue, Aug 11
Multiple Airlines Logo
1:50 pm - 7:20 pm
ORD
-
OWB
53h 30m
3 stops
Multiple Airlines Logo
9:00 am - 10:50 am
OWB
-
ORD
1h 50mnonstop
$344Multiple Airlines
Sat, Jul 25 - Mon, Jul 27
Contour Logo
11:20 am - 12:55 pm
ORD
-
OWB
1h 35mnonstop
Contour Logo
9:00 am - 10:40 am
OWB
-
ORD
1h 40mnonstop
$348Contour
Sat, Aug 1 - Thu, Aug 6
Multiple Airlines Logo
11:30 am - 1:00 pm
ORD
-
OWB
1h 30mnonstop
Multiple Airlines Logo
1:55 pm - 8:02 am
OWB
-
ORD
42h 07m
3 stops
$376Multiple Airlines
Tue, Aug 4 - Tue, Aug 11
Multiple Airlines Logo
9:34 pm - 7:20 pm
ORD
-
OWB
45h 46m
2 stops
Multiple Airlines Logo
9:00 am - 10:50 am
OWB
-
ORD
1h 50mnonstop
$385Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Owensboro flights

Get data-powered insights and trends into flights from Chicago to Owensboro to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Owensboro?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Owensboro clicked on KAYAK for each day over the last 12 months.

For Chicago to Owensboro, Wednesday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Owensboro back to Chicago, the best deals are generally found on Sunday, with Thursday being the most expensive.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Owensboro?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Owensboro, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Owensboro is November, where tickets cost $0 (return) on average. On the other hand, the most expensive months are May and July, where the average cost of round-trip tickets is $206 and $194 respectively.

Find deals

Good to know

Low season

April

Cheapest flight

$78
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Chicago to Owensboro

When to book flights from Chicago to Owensboro

Are your dates flexible? Find out the best times to travel from Chicago to Owensboro based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Owensboro flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Owensboro?

    In the last 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Owensboro was $78 for a one-way ticket and $161 for a round-trip.

  • Do I need a passport to fly between Chicago and Owensboro?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Owensboro?

    Only American Airlines offers inflight Wi-Fi service on the Chicago to Owensboro flight route.

  • Which aircraft models fly most regularly from Chicago to Owensboro?

    The Canadair (Bombardier) Regional Jet is the aircraft model that flies most regularly on the Chicago to Owensboro flight route.

  • On which days can I fly direct from Chicago to Owensboro?

    There are nonstop flights from Chicago to Owensboro on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago to Owensboro?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Owensboro.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Owensboro?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Owensboro from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Owensboro?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Owensboro with an airline and back to Chicago with another airline. Booking your flights between Chicago and OWB can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Owensboro?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Owensboro from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago O'Hare Intl Airport to Owensboro

  • Looking for a cheap flight? 25% of our users found flights on this route for $130 or less one-way.

Prefer to fly direct from Chicago to Owensboro?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago O'Hare Intl to Owensboro Daviess County.
Find which airlines fly direct from Chicago O'Hare Intl Airport to Owensboro Daviess County Airport, which days they fly and book direct flights.

Direct departures

Chicago O'Hare Intl to Owensboro Daviess County

Monday

Contour

Contour

Tuesday

Contour

Contour

Wednesday

Contour

Contour

Thursday

Contour

Contour

Friday

Contour

Contour

Saturday

Contour

Contour

Sunday

Contour

Contour

See more direct flights

Direct returns

Owensboro Daviess County to Chicago O'Hare Intl

Monday

Contour

Contour

Tuesday

Contour

Contour

Wednesday

Contour

Contour

Thursday

Contour

Contour

Friday

Contour

Contour

Saturday

Contour

Contour

Sunday

Contour

Contour

See more direct flights

Reviews of the top airline flying from Chicago to Owensboro

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Owensboro. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Owensboro? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.7
ContourOverall score based on 42 reviews
7.4Comfort
7.7Boarding
6.9Food
6.2Entertainment
8.0Crew
Airline reviews

I’ve flown Contour on 4 different flights in the last couple weeks and every one of the flights were significantly delayed. Like over 2 hours delayed. 3 of the 4 were due to maintenance and one was weather, which is beyond their control. If this continues, I will not fly them anymore. It makes me concerned that they don’t have great maintenance practices. The planes are very old and worn out and the interiors need improvement. I do like the amount of space you have between seats for legroom. They also started charging for bags recently, which I think the did when they partnered up with American Airlines as a codeshare partner. American is also a disaster of an airline so I wish they had some agreement with Delta. I am glad they offer a major airline parternership though. That is certainly giving people more opportunities. I won’t fly Contour unless they have a direct flight to where I am going. If I have to connect then I am going to take Delta. The bus at the DFW airport to get on and off the aircraft is a pain and adds so much extra time to your travel experience. I hope this is temporary while they are building a new terminal, but I don’t know.

6.0 GoodLane, Jun 2026
DFW - TUP
Read more Contour reviews

I’ve flown Contour on 4 different flights in the last couple weeks and every one of the flights were significantly delayed. Like over 2 hours delayed. 3 of the 4 were due to maintenance and one was weather, which is beyond their control. If this continues, I will not fly them anymore. It makes me concerned that they don’t have great maintenance practices. The planes are very old and worn out and the interiors need improvement. I do like the amount of space you have between seats for legroom. They also started charging for bags recently, which I think the did when they partnered up with American Airlines as a codeshare partner. American is also a disaster of an airline so I wish they had some agreement with Delta. I am glad they offer a major airline parternership though. That is certainly giving people more opportunities. I won’t fly Contour unless they have a direct flight to where I am going. If I have to connect then I am going to take Delta. The bus at the DFW airport to get on and off the aircraft is a pain and adds so much extra time to your travel experience. I hope this is temporary while they are building a new terminal, but I don’t know.

Short flight so no entertainment and none expected or appropriate. Everyone I dealt with was professional and helpful. A good experience.

Love it. No Frills but better than Spirit No Frills. It's like a simple luxury private plane especially if you've got five or six people on it because then you probably got your own section of the plane.

All the staff were amazing! The flight was quick, everything went smoothly, I have nothing but good things to say about this flight. Thank you Contour!

It was easy, efficient from start to finish. The flight attendant was amazing. Smooth ride. It was just perfect.

We had a great experience on both of our flights! Crew was great…..the ride was smooth…and checking in was easy. We will definitely fly with them again.

Not on time. Taxied around the airport for 30 MINUTES! The pilot never said a word. Ai

My luggage is missing and contour is doing a terrible service helping finding it. Unbelievable and the worst experience ever. I would love get my money back.

It’s the only flight connecting Marion to Chicago, I do appreciate that it was available!

The boarding procedure is as easy and the crew very friendly.

Everything you need to know for your flight from Chicago to Owensboro

Information on your arrival and departure airports

Chicago (ORD)
Owensboro (OWB)