$77 Find Cheap Flights to Madisonville - Compare and Save

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Flight Deals

Cheap Flights to Madisonville

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Madisonville

Sat, Oct 3 - Sat, Oct 10
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$156Contour
Sat, Oct 3 - Sat, Oct 10
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$160Contour
Sat, Oct 3 - Sat, Oct 10
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$163Contour
Wed, Sep 23 - Sun, Sep 27
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$163Contour
Sat, Sep 19 - Sun, Sep 20
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$163Contour
Sun, Sep 20 - Sat, Sep 26
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$163Contour
Sat, Sep 19 - Wed, Sep 23
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$163Contour
Sun, Nov 1 - Thu, Nov 5
United Airlines Logo
9:30 pm - 11:05 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 35mnonstop
United Airlines Logo
2:25 pm - 4:15 pmOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$196United Airlines
Mon, Oct 26 - Thu, Oct 29
United Airlines Logo
9:30 pm - 11:05 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 35mnonstop
United Airlines Logo
2:25 pm - 4:15 pmOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$236United Airlines
Sat, Oct 3 - Sat, Oct 10
Multiple Airlines Logo
3:50 pm - 7:20 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
27h 30m2 stops Orlando Charlotte Douglas
Multiple Airlines Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$315Multiple Airlines
Useful Info

Good to know - Book Cheap Madisonville Plane Tickets

Low season

April

Cheapest flight

$77
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Chicago to Owensboro

FAQs - booking Madisonville flights

  • How long is the flight to Madisonville?

    Flights from Chicago1h 30m
    Flights from Chicago O'Hare Intl Airport1h 30m

  • Which airlines fly to Owensboro?

    Many airlines fly to Owensboro, the most common ones being Southwest, American Airlines, and Delta. See the amount of flights per week for popular airlines flying to Owensboro.

  • How to fly to Madisonville?

    You cannot fly directly to Madisonville. KAYAK recommends you fly to Owensboro Daviess County (OWB) (33.92 miles from Madisonville). From there you can rent a car or get a taxi.

  • What airports are near Madisonville?

    The closest airport is Owensboro Daviess County (OWB) (33.92 mi). Other nearby airports are Evansville Dress Regional (EVV) (48.96 mi), Paducah Barkley Regional (PAH) (72.5 mi), Marion Williamson County (MWA) (87.9 mi) or Nashville Intl (BNA) (94.85 mi). KAYAK recommends you fly to Owensboro Daviess County.

  • How far is Owensboro Daviess County Airport from central Owensboro?

    There are 4 miles between Owensboro city center and Owensboro Daviess County Airport.

  • What is the name of Owensboro’s airport?

    All flights to Owensboro land at Owensboro Daviess County Airport. The airport code is OWB,and it can also be referred to as Daviess Count or Daviess County.

  • How does KAYAK find such low prices on flights to Madisonville?

    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 to Madisonville.

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

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

  • What is the Hacker Fare option on flights to Madisonville?

    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 Madisonville with an airline and back with another airline.

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

    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 Madisonville up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Madisonville

  • There is no major airport in Madisonville. It is instead served by Owensboro Daviess County Airport.
  • Looking for a cheap flight? 25% of our users found flights on this route for $134 or less one-way and $223 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Madisonville flight deals.

Reviews of the top airline flying to Madisonville

 
Need help choosing which airline to fly with from the United States to Madisonville? 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.
7.5
ContourOverall score based on 43 reviews
7.5Boarding
6.8Food
7.8Crew
6.1Entertainment
7.3Comfort
Airline reviews

You could have NOT left me and my family high and dry by not completing the reservation changes because they no longer have the contract from Phoenix AZ to Moab Utah. There wasn't even a ticket agent for Contour in Phoenix to talk to. Cost my an additional $1600. to rent a vehicle to get my family to Utah. Now I'm left with trying to have someone make it right financially. I'm not optimistic..........

2.0 MediocreBarbra, Aug 2026
Read more Contour reviews

You could have NOT left me and my family high and dry by not completing the reservation changes because they no longer have the contract from Phoenix AZ to Moab Utah. There wasn't even a ticket agent for Contour in Phoenix to talk to. Cost my an additional $1600. to rent a vehicle to get my family to Utah. Now I'm left with trying to have someone make it right financially. I'm not optimistic..........

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.

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

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

More options for your flight to Madisonville