$31 Find Cheap Flights from Illinois to Kentucky

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Low seasonJanuary
High seasonMay
Cheapest flight$31
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 1% increase in price.
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 $131.

  • 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 $462 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 $276 on average. Morning departures are around 11% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $311.

  • 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 $226 (return) on average. On the other hand, the most expensive months are February and March, when the average cost of round-trip tickets is $416 and $403 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 6h 39m, covering a distance of 366 miles. The shortest route is St. Louis (STL) to Nashville (BNA) with an average flight time of 1h 10m.

  • 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 (23%) and Cincinnati (10%). Searches for flights to Louisville (7%), to Lexington (5%) and to Blountville (1%) are also popular.

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 4294 reviews
8.0Comfort
8.2Boarding
7.1Food
8.6Crew
7.6Entertainment
Airline reviews

It is southwest seat was ok. Not the most comfortable seat

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

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.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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.

This is a great airline for what it is. You get 1 checked bag included per passenger and the space per seat is incredible. It’s an E135 aircraft that is configured to seat 50 people but they have removed 20 seats and only seat 30 so you have a ton of legroom. They are doing things right and have a great product for what it is. It’s not going to knock your socks off in experience overall but the plane, although dates, was nice and clean and the crew was great. The flights were on time and super efficient. Will travel them again. I am a frequent traveler on all the larger airlines and this was just as good as any regional carrier, if not better. I expect big things out of Contour in the years to come.

Not waiting on the tarmac for an hour and 20 minutes

Book cheap flights from Illinois to Kentucky

Recent round-trip flight deals

6/3Tue
1 stop
9h 36mORD-BNA
6/5Thu
nonstop
1h 49mBNA-ORD
$74
6/2Mon
nonstop
1h 32mORD-BNA
6/5Thu
nonstop
1h 49mBNA-ORD
$75
5/16Fri
nonstopSpirit Airlines
1h 32mORD-BNA
5/19Mon
nonstopSpirit Airlines
1h 57mBNA-ORD
$77
5/16Fri
nonstopSpirit Airlines
1h 32mORD-BNA
5/19Mon
nonstopSpirit Airlines
1h 57mBNA-ORD
$80
5/30Fri
nonstopSouthwest
1h 30mMDW-BNA
6/2Mon
nonstopSouthwest
1h 35mBNA-MDW
$145
7/15Tue
nonstopSouthwest
1h 30mMDW-BNA
7/18Fri
nonstopSouthwest
1h 35mBNA-MDW
$152
9/6Sat
nonstopAmerican Airlines
1h 30mORD-BNA
9/10Wed
nonstopAmerican Airlines
1h 52mBNA-ORD
$159
5/21Wed
nonstopAmerican Airlines
1h 39mORD-BNA
5/23Fri
nonstopAmerican Airlines
1h 53mBNA-ORD
$162
5/27Tue
nonstopUnited Airlines
1h 45mORD-TYS
6/3Tue
nonstopUnited Airlines
2h 02mTYS-ORD
$189
6/3Tue
nonstopUnited Airlines
1h 31mORD-SDF
6/4Wed
nonstopUnited Airlines
1h 37mSDF-ORD
$201

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Recent one-way flight deals

6/3Tue
1 stopSpirit Airlines
9h 36mORD-BNA
$31
6/2Mon
nonstopSpirit Airlines
1h 32mORD-BNA
$32
5/29Thu
nonstopFrontier
1h 36mORD-BNA
$39
6/30Mon
nonstopFrontier
1h 44mORD-BNA
$42
6/19Thu
nonstopUnited Airlines
1h 55mORD-BNA
$73
6/19Thu
nonstopSouthwest
1h 30mMDW-BNA
$73
7/26Sat
1 stopSouthwest
3h 05mMDW-BNA
$78
8/19Tue
nonstopAmerican Airlines
1h 30mORD-BNA
$80
5/29Thu
nonstopAmerican Airlines
1h 36mORD-SDF
$90
6/24Tue
nonstopUnited Airlines
1h 31mORD-SDF
$101

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Last minute flights from Illinois to Kentucky

Last minute flight, train and bus deals

5/4Sun
multi-stopFrontier
14h 19mORD-CVG
5/5Mon
multi-stopFrontier
11h 36mCVG-ORD
$202
5/3Sat
multi-stopFrontier
18h 21mORD-CVG
5/11Sun
multi-stopFrontier
11h 40mCVG-ORD
$230
5/3Sat
nonstopUnited Airlines
1h 30mORD-LEX
5/6Tue
nonstopUnited Airlines
1h 47mLEX-ORD
$252
5/1Thu
multi-stopSouthern / Mokulele
4h 05mSTL-BNA
5/4Sun
multi-stopSouthern / Mokulele
4h 06mBNA-STL
$252
5/3Sat
nonstopAmerican Airlines
1h 26mORD-LEX
5/6Tue
multi-stopAmerican Airlines
5h 27mLEX-ORD
$262
5/1Thu
multi-stopSouthern / Mokulele
4h 05mSTL-BNA
5/4Sun
multi-stopSouthern / Mokulele
4h 06mBNA-STL
$272
5/1Thu
nonstopAmerican Airlines
1h 31mORD-LEX
5/3Sat
nonstopAmerican Airlines
1h 39mLEX-ORD
$279
5/4Sun
nonstopUnited Airlines
1h 30mORD-LEX
5/7Wed
nonstopUnited Airlines
1h 45mLEX-ORD
$289
5/5Mon
nonstopSouthwest
1h 40mORD-BNA
5/8Thu
nonstopSouthwest
1h 55mBNA-ORD
$430
5/5Mon
nonstopSouthwest
1h 30mMDW-BNA
5/8Thu
nonstopSouthwest
1h 35mBNA-MDW
$430

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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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