$39 Find Cheap Flights from Illinois to Kentucky

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Low seasonJanuary
Cheapest flight$39
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago O'Hare Airport to Nashville

FAQs for booking flights from Illinois to Kentucky

  • How does KAYAK find such low prices on flights from Illinois to Kentucky?

    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 from Illinois to Kentucky.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Kentucky?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Kentucky is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Illinois to Kentucky?

    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 from Illinois to Kentucky 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 from Illinois to Kentucky?

    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 from Illinois to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Kentucky?

    Illinois and Kentucky are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (69 flights per week), Alaska Airlines (46 flights per week), and American Airlines (46 flights per week).

  • How many airports are there in Kentucky?

    There are 4 airports in Kentucky. The busiest airport is Louisville Airport (SDF), with 67% of all flights arriving there.

  • Which is the cheapest airport to fly into in Kentucky?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Kentucky is Owensboro Daviess County Airport (OWB), with an average flight price of $130.

  • What is the cheapest day to fly to Kentucky?

    Based on KAYAK data, the cheapest day to fly to Kentucky is Saturday where round-trip tickets can be as cheap as $250. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $575 on average.

  • What is the cheapest time of day to fly to Kentucky?

    The cheapest time of day to fly to Kentucky is generally in the afternoon, when round-trip flights cost $285 on average. Morning departures are around 7% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the morning, which is peak travel time and where the average cost of a ticket is $319.

  • What is the cheapest flight to Kentucky?

    The cheapest ticket to Kentucky from Illinois found in the last 72 hours was to Louisville, at $97 round-trip. The most popular route is Chicago Midway Airport (MDW) to Louisville (SDF) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $97.

  • What is the cheapest month to fly from Illinois to Kentucky?

    The cheapest month for flights from Illinois to Kentucky is August, when tickets cost $186 (return) on average. On the other hand, the most expensive months are September and March, when the average cost of round-trip tickets is $535 and $423 respectively.

  • How far in advance should I book a flight from Illinois to Kentucky?

    To get a below average price on the flight from Illinois to Kentucky, you should book around 4 weeks before departure, which saves you about 62% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

  • How many cities have direct flights to Kentucky?

    From Illinois, there are direct flights to Kentucky from 1 city. This city is Chicago and there are 444 direct flights each week.

  • How many direct flights to Kentucky are there each day?

    There are around 64 direct flights from within Illinois to Kentucky every day. Most flights (43%) depart in the evening.

  • How many direct flights to Kentucky are there each week?

    Each week there are around 444 direct flights from within Illinois to Kentucky. The most common day for departures is Monday, with 15% of flights taking off on this day.

  • How long is the flight to Kentucky?

    An average nonstop flight from Illinois to Kentucky takes 5h 54m, covering a distance of 366 miles. The shortest route is Chicago Midway Airport (MDW) to Cincinnati (CVG) with an average flight time of 1h 05m.

  • How many long-haul flights are there to Kentucky each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Kentucky. Instead, there are 444 short-haul flights (up to 3 hour flight duration), with the most arriving from Chicago.

  • What are the most popular destinations in Kentucky?

    Based on KAYAK flight searches, the most popular destination is Nashville (55% of total searches to Kentucky). The next most popular destinations are Cincinnati (17%) and Knoxville (15%). Searches for flights to Lexington (6%), to Louisville (6%) and to Blountville (1%) are also popular.

Reviews of the top 4 airlines serving from Illinois to Kentucky

 
Need help choosing which airline to fly with from Illinois to Kentucky? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Everything was fine. Flight boarded and departed on time. Seating was spacious enough for my carryon to fit under the seat in front of me. No complaints at all. Flight even arrived early.

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

We had a great experience on both of our flights! Crew was great…..the ride was smooth…and checking in was easy. We will definitely fly with them again.

This was my first time flying with Contour and the Greenbrier Valley Airport. It both were excellent and the price couldn’t be beat!

Not on time. Taxied around the airport for 30 MINUTES! The pilot never said a word. Ai

Great flight, professional crew, convenient and interesting nonstop routes. Had trouble with getting precheck listed on boarding pass, but found that customer service was remarkably responsive via email — unheard of with other carriers. A great experience overalll.

I felt like a sardine in my seat. We all did. The plane was so small that I hit my head on the roof when I stood up from my seat. The service was good and the crew were nice.

My luggage is missing and contour is doing a terrible service helping finding it. Unbelievable and the worst experience ever. I would love get my money back.

Flight was cancelled, but they got him on an earlier delayed rescheduled one. Arrived Chicago 2 hours later than expected but long layover so it worked.

Crew very helpful, weather made the flight less than optimal.

Flight was fine. I just forgot how smaller planes have more dips and seats in high winds.

It’s the only flight connecting Marion to Chicago, I do appreciate that it was available!

Everything you need to know for your flight to Kentucky

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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