Cheap Flights from Chicago to Kentucky from 89 € Return

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.

Louisville.89 € per passenger.Departing Thu, 28 Aug, returning Wed, 3 Sep.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 28 Aug, arriving in Louisville Muhammad Ali International .Inbound direct flight with United departs from Louisville Muhammad Ali International on Wed, 3 Sep, arriving in Chicago O'Hare International.Price includes taxes and charges.From 89 €, select.

Owensboro.121 € per passenger.Departing Thu, 1 May, returning Mon, 5 May.Return flight with Contour Airlines.Outbound direct flight with Contour Airlines departs from Chicago O'Hare International on Thu, 1 May, arriving in Owensboro.Inbound direct flight with Contour Airlines departs from Owensboro on Mon, 5 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From 121 €, select.

Lexington.172 € per passenger.Departing Wed, 25 Jun, returning Sat, 19 Jul.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 25 Jun, arriving in Lexington Blue Grass.Inbound direct flight with United departs from Lexington Blue Grass on Sat, 19 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 172 €, select.

Flying from Chicago to Kentucky

Arm yourself with these facts on the fly.

Cheapest flight found	89 €, Louisville
Cheapest month to fly	August
Average flight time	1 hr, 22 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	Alaska 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 89 € and one-way tickets from 44 € 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 Louisville

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

Fly in May

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

Fly on a Thursday

From our data, we can see that Thursday seems to be the cheapest time to fly from Chicago to Kentucky.

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 Chicago 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 89 € is the best price. This is good, compared to the average Kentucky ticket price of 193 €.

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

The cheapest month to fly from Chicago to Owensboro Airport is currently May. The cheapest month to fly from Chicago to Louisville Muhammad Ali International Airport is usually August. And the cheapest month to fly from Chicago to Lexington Blue Grass Airport is usually June.

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, 28 August 2025.

Are there any direct flights from Chicago to Kentucky?

Chicago O'Hare International Airport offers 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 Louisville. The cheapest airport serving Louisville at the moment is Louisville Muhammad Ali International .