$49 Find Cheap Flights from Illinois to Kentucky

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Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds with an average 4% drop in price.
Flight from St. Louis 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 (98 flights per week), American Airlines (69 flights per week), and Alaska 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 68% 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 $115.

  • 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 Sunday, where round-trip prices are $467 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 morning, when round-trip flights cost $295 on average. Morning departures are around 16% cheaper than evening flights, on average. The most expensive time of day to fly to Kentucky is generally at night, which is peak travel time and where the average cost of a ticket is $359.

  • What is the cheapest flight to Kentucky?

    The cheapest ticket to Kentucky from Illinois found in the last 72 hours was to Owensboro, at $59 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 $241.

  • 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 February and April, when the average cost of round-trip tickets is $508 and $443 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 60% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 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 536 direct flights each week.

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

    There are around 77 direct flights from within Illinois to Kentucky every day. Most flights (39%) depart in the evening.

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

    Each week there are around 536 direct flights from within Illinois to Kentucky. The most common day for departures is Friday, with 16% of flights taking off on this day.

  • How long is the flight to Kentucky?

    An average nonstop flight from Illinois to Kentucky takes 5h 15m, 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 536 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 (63% of total searches to Kentucky). The next most popular destinations are Knoxville (16%) and Louisville (9%). Searches for flights to Cincinnati (6%), to Lexington (4%) 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 4328 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

The seat was not comfortable. 1D. My back was sore all night and the next day.

8.0 ExcellentJolene, Apr 2026
LAS - DAL
Read more Southwest reviews

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

Short flight so no entertainment and none expected or appropriate. Everyone I dealt with was professional and helpful. A good experience.

Love it. No Frills but better than Spirit No Frills. It's like a simple luxury private plane especially if you've got five or six people on it because then you probably got your own section of the plane.

All the staff were amazing! The flight was quick, everything went smoothly, I have nothing but good things to say about this flight. Thank you Contour!

It was easy, efficient from start to finish. The flight attendant was amazing. Smooth ride. It was just perfect.

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.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

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.