$28 Find Cheap Flights from Illinois to Kentucky

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Kentucky

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info

Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$28
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 0% 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 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 $69.

  • 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 $257. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $535 on average.

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

    The cheapest time of day to fly to Kentucky is generally at night, when round-trip flights cost $283 on average. Morning departures are around 8% 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 $321.

  • What is the cheapest flight to Kentucky?

    The cheapest ticket to Kentucky from Illinois found in the last 72 hours was to Louisville, at $77 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 $77.

  • 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 $216 (return) on average. On the other hand, the most expensive months are September and February, when the average cost of round-trip tickets is $434 and $416 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. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

  • How long is the flight to Kentucky?

    An average nonstop flight from Illinois to Kentucky takes 5h 51m, 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.

  • What are the most popular destinations in Kentucky?

    Based on KAYAK flight searches, the most popular destination is Nashville (52% of total searches to Kentucky). The next most popular destinations are Knoxville (25%) and Cincinnati (13%). Searches for flights to Louisville (5%), 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 4250 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.6Entertainment
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

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.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

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!

The flight was delayed and then less than 30 mins before boarding they cancelled the flight when clearly they had to have known earlier that they were going to have to cancel. There was only one person there available to talk to and all he could do was tell us to call reservations our self. Due to high call volume I waited 2 hours to even get rebooked on a flight to a different city where I would still have to drive 1 hr to my destination, only option for me. While waiting to talk to reservations people were getting emails with new flight info and the flights were days out and sone even a week out. . I did not get compensated in anyway after having spent all day at the airpot, not even a food voucher. Very disappointed, terrible experience.

Information regarding the delayed flight could have been better, and the Contour airlines app needs some serious updates. But overall, the crew was great and the flight was uneventful.

The boarding procedure is as easy and the crew very friendly.

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.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

Book cheap flights from Illinois to Kentucky

Recent round-trip flight deals

8/8Fri
nonstopFrontier
1h 39mORD-BNA
8/11Mon
nonstopFrontier
2h 04mBNA-ORD
$51
8/11Mon
nonstopSpirit Airlines
1h 29mORD-BNA
8/11Mon
nonstopSpirit Airlines
2h 03mBNA-ORD
$60
7/31Thu
nonstop
1h 39mORD-BNA
8/4Mon
nonstop
2h 03mBNA-ORD
$80
7/25Fri
nonstop
1h 39mORD-BNA
7/28Mon
nonstop
2h 03mBNA-ORD
$83
8/6Wed
nonstopUnited Airlines
1h 26mORD-CVG
8/7Thu
nonstopUnited Airlines
1h 35mCVG-ORD
$91
8/5Tue
nonstopUnited Airlines
1h 31mORD-SDF
8/7Thu
nonstopUnited Airlines
1h 37mSDF-ORD
$91
8/11Mon
nonstopSouthwest
1h 10mMDW-CVG
8/12Tue
nonstopSouthwest
1h 10mCVG-MDW
$91
9/5Fri
nonstopSouthwest
1h 35mORD-BNA
9/8Mon
nonstopSouthwest
1h 50mBNA-ORD
$91
8/20Wed
nonstopAmerican Airlines
1h 25mORD-SDF
8/27Wed
nonstopAmerican Airlines
1h 46mSDF-ORD
$92
8/13Wed
nonstopAmerican Airlines
1h 18mORD-CVG
8/16Sat
nonstopAmerican Airlines
1h 31mCVG-ORD
$101

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/11Mon
nonstopSpirit Airlines
1h 29mORD-BNA
$28
8/11Mon
nonstopSpirit Airlines
1h 29mORD-BNA
$32
7/21Mon
nonstopFrontier
1h 39mORD-BNA
$39
9/1Mon
nonstopFrontier
1h 51mORD-BNA
$40
11/8Sat
nonstopUnited Airlines
1h 19mORD-CVG
$46
10/8Wed
nonstopUnited Airlines
1h 36mORD-SDF
$46
8/18Mon
nonstopSouthwest
1h 10mMDW-CVG
$46
8/22Fri
nonstopSouthwest
1h 35mORD-BNA
$46
8/7Thu
nonstopAmerican Airlines
1h 18mORD-CVG
$60
11/13Thu
nonstopAmerican Airlines
1h 43mORD-BNA
$60

Search by stops

Search by airline

Search by price

Last minute flights from Illinois to Kentucky

Last minute flight, train and bus deals

7/14Mon
nonstopSpirit Airlines
1h 29mORD-BNA
7/18Fri
nonstopSpirit Airlines
2h 03mBNA-ORD
$106
7/14Mon
nonstopSpirit Airlines
1h 29mORD-BNA
7/17Thu
multi-stopSpirit Airlines
7h 07mBNA-ORD
$123
7/11Fri
nonstop
1h 29mORD-BNA
7/14Mon
nonstop
2h 04mBNA-ORD
$125
7/14Mon
nonstop
1h 39mORD-BNA
7/16Wed
multi-stop
6h 30mBNA-ORD
$129
7/12Sat
nonstopAmerican Airlines
1h 47mORD-TYS
7/16Wed
nonstopAmerican Airlines
1h 58mTYS-ORD
$264
7/12Sat
multi-stopAmerican Airlines
5h 43mORD-TYS
7/16Wed
nonstopAmerican Airlines
1h 58mTYS-ORD
$274
7/14Mon
nonstopSouthwest
1h 30mMDW-BNA
7/18Fri
nonstopSouthwest
1h 35mBNA-MDW
$337
7/14Mon
nonstopSouthwest
1h 30mMDW-BNA
7/18Fri
multi-stopSouthwest
5h 35mBNA-MDW
$347
7/11Fri
nonstopUnited Airlines
1h 45mORD-TYS
7/13Sun
nonstopUnited Airlines
1h 57mTYS-ORD
$409
7/11Fri
nonstopUnited Airlines
1h 27mORD-CVG
8/4Mon
nonstopUnited Airlines
1h 44mCVG-ORD
$411

Search by stops

Search by airline

Search by price

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.