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Flights from Chicago to Kentucky

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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, 8 May, returning Mon, 12 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 8 May, arriving in Louisville Muhammad Ali International .Inbound direct flight with Southwest Airlines departs from Louisville Muhammad Ali International on Mon, 12 May, arriving in Chicago Midway.Price includes taxes and charges.From SAR 363, select.
Owensboro.SAR 538 per passenger.Departing Thu, 12 Jun, returning Fri, 13 Jun.Return flight with Contour Airlines.Outbound direct flight with Contour Airlines departs from Chicago O'Hare International on Thu, 12 Jun, arriving in Owensboro.Inbound direct flight with Contour Airlines departs from Owensboro on Fri, 13 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 538, select.
Lexington.SAR 707 per passenger.Departing Thu, 22 May, returning Sun, 25 May.Return flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Thu, 22 May, arriving in Lexington Blue Grass.Inbound direct flight with American Airlines departs from Lexington Blue Grass on Sun, 25 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 707, select.
Paducah.SAR 1,735 per passenger.Departing Sun, 1 Jun, returning Sun, 8 Jun.Return flight with Contour Airlines.Outbound indirect flight with Contour Airlines, departs from Chicago O'Hare International on Sun, 1 Jun, arriving in Paducah.Inbound indirect flight with Contour Airlines, departs from Paducah on Sun, 8 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 1,735, select.

Flying from Chicago to Kentucky

Arm yourself with these facts on the fly.
Cheapest flight foundSAR 363, Louisville
Cheapest month to flyMay
Average flight time1 hr, 22 mins
Cheapest airport to fly fromChicago Midway
Most popular airlineAlaska Airlines

Frequently asked questions

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 811.
The cheapest month to fly from Chicago to Paducah Airport is usually June. The cheapest month to fly from Chicago to Louisville Muhammad Ali International Airport is usually May. The cheapest month to fly from Chicago to Lexington Blue Grass Airport is usually May. And the cheapest month to fly from Chicago to Owensboro Airport is usually June.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Kentucky on Thursday, 8 May 2025.
Chicago Midway Airport and Chicago O'Hare International Airport all offer direct flights to Kentucky.
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 .
The average flight time between Chicago and Kentucky is 1 hour and 21 minutes.