Flights from Chicago to Kentucky

Flight deals from Chicago to Kentucky

Looking for cheap tickets from Chicago to Kentucky, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.

Owensboro.Rs17,217 per passenger.Departing Tue, 31 Mar.One-way flight with Contour Airlines.Outbound direct flight with Contour Airlines departs from Chicago O'Hare International on Tue, 31 Mar, arriving in Owensboro.Price includes taxes and charges.From Rs17,217, select.

Louisville.Rs20,495 per passenger.Departing Sat, 14 Mar.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 14 Mar, arriving in Louisville Muhammad Ali International.Price includes taxes and charges.From Rs20,495, select.

Lexington.Rs31,749 per passenger.Departing Wed, 18 Feb.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 18 Feb, arriving in Lexington Blue Grass.Price includes taxes and charges.From Rs31,749, select.

Paducah.Rs41,073 per passenger.Departing Fri, 15 May.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 15 May, arriving in Paducah.Price includes taxes and charges.From Rs41,073, select.

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Flying from Chicago to Kentucky

Arm yourself with these facts on the fly.

Cheapest flight found	Rs17,217
Cheapest month to fly	March
Average flight time	1 hr, 23 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	American Airlines

How to find cheap flights from Chicago to Kentucky

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Kentucky. Other savvy travellers recently found return flights from Rs33,772 and one-way tickets from Rs17,217 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into Owensboro

At the moment, the lowest priced flight tickets to Kentucky are from Chicago O'Hare International Airport to Owensboro Airport.

Fly in March

We crunched the flight calendar and found the cheapest time to fly from Chicago to Kentucky is currently March.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Kentucky.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Kentucky go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Kentucky to Kentucky flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Kentucky flight price?

We looked at all of the upcoming return flights from Chicago to Kentucky we could find over the next 12 months. It looks like Rs33,836 is the best price. This is good, compared to the average Kentucky ticket price of Rs47,890.

What is the cheapest month to fly from Chicago to Kentucky?

The cheapest month to fly from Chicago to Lexington Blue Grass Airport is usually March. The cheapest month to fly from Chicago to Owensboro Airport is usually March. The cheapest month to fly from Chicago to Louisville Muhammad Ali International Airport is usually April. And the cheapest month to fly from Chicago to Paducah Airport is usually March.

Which upcoming date is cheapest to fly from Chicago to Kentucky on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Kentucky on Thursday, 12 March 2026.

Are there any direct flights from Chicago to Kentucky?

Chicago O'Hare International Airport and Chicago Midway Airport all offer direct flights to Kentucky.

If I'm flying from Chicago, where in Kentucky is cheapest to fly into?

If you're flying from Chicago, the cheapest city in Kentucky to fly into is Owensboro. The cheapest airport serving Owensboro at the moment is Owensboro.