How long is the flight to Madisonville?

Flights from Chicago - 1h 30m Flights from Chicago O'Hare Intl Airport - 1h 30m

What is the cheapest flight to Owensboro?

In the last 5 days, the cheapest flight deal to Owensboro was found on the route from Chicago , at $159 return . The most popular connection is from Chicago to Owensboro and KAYAK users have found round-trip deals for as low as $159 in the last 5 days.

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.

$78 CHEAP FLIGHTS to Madisonville (OWB)

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Cheapest round-trip

$159

Typical prices: $148-$198

Contour

Tue 9/8Wed 9/9

ORD - OWB • Non-stop

Cheapest one-way

$78

Typical prices: $71-$130

Contour

Thu 8/27

ORD - OWB • Non-stop

Arrival airport

Owensboro (OWB)

You can't fly directly to Madisonville. It is served by Owensboro (OWB), located 33.9 miles from Madisonville.

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Flight Deals

Cheap Flights to Madisonville

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

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One-way

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Recent round-trip flight deals to Madisonville

Tue, Sep 8 - Wed, Sep 9

11:30 am - 1:00 pm

ORD

OWB

1h 30mnonstop

9:00 am - 10:50 am

OWB

ORD

1h 50mnonstop

$159Contour

Fri, Aug 14 - Sun, Aug 16

11:30 am - 1:00 pm

ORD

OWB

1h 30mnonstop

9:00 am - 10:50 am

OWB

ORD

1h 50mnonstop

$160Contour

Tue, Sep 8 - Wed, Sep 9

11:30 am - 1:00 pm

ORD

OWB

1h 30mnonstop

9:00 am - 10:50 am

OWB

ORD

1h 50mnonstop

$161Contour

Thu, Aug 6 - Sun, Aug 9

11:30 am - 1:00 pm

ORD

OWB

1h 30mnonstop

9:00 am - 10:50 am

OWB

ORD

1h 50mnonstop

$178Contour

Sun, Aug 2 - Thu, Aug 6

11:30 am - 1:00 pm

ORD

OWB

1h 30mnonstop

9:00 am - 10:50 am

OWB

ORD

1h 50mnonstop

$249Contour

Thu, Nov 12 - Sun, Nov 15

9:20 pm - 10:55 pm

ORD

OWB

1h 35mnonstop

2:25 pm - 4:15 pm

OWB

ORD

1h 50mnonstop

$297United Airlines

Mon, Aug 3 - Fri, Aug 7

11:30 am - 1:00 pm

ORD

OWB

1h 30mnonstop

9:00 am - 10:50 am

OWB

ORD

1h 50mnonstop

$298Contour

Thu, Nov 5 - Sun, Nov 8

10:33 am - 1:40 pm

RDU

OWB

4h 07m

1 stop

8:45 am - 2:08 pm

OWB

RDU

4h 23m

1 stop

$337United Airlines

Sat, Nov 14 - Sat, Nov 21

9:20 pm - 10:55 pm

ORD

OWB

1h 35mnonstop

2:25 pm - 4:15 pm

OWB

ORD

1h 50mnonstop

$347United Airlines

Tue, Sep 8 - Wed, Sep 9

11:30 am - 1:00 pm

ORD

OWB

1h 30mnonstop

1:55 pm - 12:41 pm

OWB

ORD

22h 46m

3 stops

$375Multiple Airlines

Useful Info

Low season	April
High season	August
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

How long is the flight to Madisonville?
Flights from Chicago 1h 30m
Flights from Chicago O'Hare Intl Airport 1h 30m
What is the cheapest flight to Owensboro?
In the last 5 days, the cheapest flight deal to Owensboro was found on the route from Chicago, at $159 return. The most popular connection is from Chicago to Owensboro and KAYAK users have found round-trip deals for as low as $159 in the last 5 days.
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.

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 $130 or less one-way and $187 or less round-trip.
Enter your preferred departure airport and travel dates into the search form above to unlock the latest Madisonville flight deals.

7.7

ContourOverall score based on 42 reviews

7.4Comfort

7.7Boarding

6.9Food

8.0Crew

6.2Entertainment

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