ORD - OWB

$53 Find Cheap Flights from Chicago to Owensboro

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 1/4. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Owensboro

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Owensboro, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Owensboro, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$100
Contour
Sat 12/13Wed 12/17
ORD - OWB • Non-stop
Cheapest one-way
$53
Typical prices: $142-$145
Contour
Sun 1/4
ORD - OWB • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
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

Sat, Dec 13 - Wed, Dec 17
Contour Logo
9:40 am - 11:10 amORD-OWB
1h 30mnonstop
Contour Logo
8:40 am - 10:15 amOWB-ORD
1h 35mnonstop
$100Contour
Find Deal
Sat, Dec 13 - Sun, Dec 14
Contour Logo
9:40 am - 11:10 amORD-OWB
1h 30mnonstop
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8:40 am - 10:15 amOWB-ORD
1h 35mnonstop
$101Contour
Find Deal
Fri, Dec 26 - Thu, Jan 1
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5:30 pm - 7:00 pmORD-OWB
1h 30mnonstop
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8:40 am - 10:15 amOWB-ORD
1h 35mnonstop
$118Contour
Find Deal
Sun, Jan 18 - Thu, Jan 22
Contour Logo
10:55 am - 12:25 pmORD-OWB
1h 30mnonstop
Contour Logo
8:40 am - 10:15 amOWB-ORD
1h 35mnonstop
$119Contour
Find Deal
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 Friday is the most expensive. Flying from Owensboro back to Chicago, the best deals are generally found on Monday, with Friday being the most expensive.

Find deals

Good to know

Low seasonDecember
Cheapest flight$53
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 18% 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 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Owensboro was $53 for a one-way ticket and $100 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 $148 or less round-trip.

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

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Wednesday

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Direct returns

Owensboro Daviess County to Chicago O'Hare Intl

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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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.
7.6
ContourOverall score based on 42 reviews
6.2Entertainment
7.9Crew
6.9Food
7.6Boarding
7.3Comfort
Airline reviews

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

10.0 ExcellentAnonymous, Nov 2025TSM - DEN
Read more Contour reviews

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.

This was my first time flying with Contour and the Greenbrier Valley Airport. It both were excellent and the price couldn’t be beat!

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

Great flight, professional crew, convenient and interesting nonstop routes. Had trouble with getting precheck listed on boarding pass, but found that customer service was remarkably responsive via email — unheard of with other carriers. A great experience overalll.

I felt like a sardine in my seat. We all did. The plane was so small that I hit my head on the roof when I stood up from my seat. The service was good and the crew were nice.

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.

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

Information on your arrival and departure airports

Chicago (ORD)
Owensboro (OWB)