Cheap Flights from Chicago to Kentucky from SAR 363 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.SAR 363 per passenger.Departing Thu, 25 Dec, returning Wed, 7 Jan.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 25 Dec, arriving in Louisville Muhammad Ali International.Inbound direct flight with United departs from Louisville Muhammad Ali International on Wed, 7 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 363, select.

Owensboro.SAR 555 per passenger.Departing Sat, 1 Nov, returning Sun, 2 Nov.Return flight with Contour Airlines.Outbound direct flight with Contour Airlines departs from Chicago O'Hare International on Sat, 1 Nov, arriving in Owensboro.Inbound direct flight with Contour Airlines departs from Owensboro on Sun, 2 Nov, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 555, select.

Lexington.SAR 709 per passenger.Departing Thu, 15 Jan, returning Mon, 19 Jan.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 15 Jan, arriving in Lexington Blue Grass.Inbound direct flight with United departs from Lexington Blue Grass on Mon, 19 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 709, select.

Paducah.SAR 1,735 per passenger.Departing Fri, 10 Oct, returning Tue, 14 Oct.Return flight with Frontier Airlines and Contour Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 10 Oct, arriving in Paducah.Inbound indirect flight with Contour Airlines, departs from Paducah on Tue, 14 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 1,735, select.

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Flying from Chicago to Kentucky

Arm yourself with these facts on the fly.

Cheapest flight found	SAR 363
Cheapest month to fly	December
Average flight time	1 hr, 22 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 SAR 363 and one-way tickets from SAR 144 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 Muhammad Ali International

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 December

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

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 SAR 363 is the best price. This is good, compared to the average Kentucky ticket price of SAR 841.

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

The cheapest month to fly from Chicago to Paducah Airport is usually October. The cheapest month to fly from Chicago to Louisville Muhammad Ali International Airport is usually December. The cheapest month to fly from Chicago to Owensboro Airport is usually November. And the cheapest month to fly from Chicago to Lexington Blue Grass Airport is usually January.

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, 25 December 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.