$38 Find Cheap Flights from Kentucky to Illinois

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Low seasonJanuary
High seasonMay
Cheapest flight$38
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Nashville to Chicago O'Hare Airport

FAQs for booking flights from Kentucky to Illinois

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

    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 Kentucky to Illinois.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Kentucky to Illinois 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 Kentucky to Illinois?

    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 Kentucky to Illinois 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 Kentucky to Illinois?

    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 Kentucky to Illinois 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 Illinois?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago Midway Airport (MDW), with an average flight price of $239.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Thursday where round-trip tickets can be as cheap as $505. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $725 on average.

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

    The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $514 on average. Morning departures are around 45% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $952.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Kentucky found in the last 72 hours was to Chicago O'Hare Intl Airport, at $133 round-trip. The most popular route is Lexington (LEX) to Chicago O'Hare Intl Airport (ORD) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $133.

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

    The cheapest month for flights from Kentucky to Illinois is February, when tickets cost $123 (return) on average. On the other hand, the most expensive months are October and May, when the average cost of round-trip tickets is $216 and $165 respectively.

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

    To get a below average price on the flight from Kentucky to Illinois, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

  • How long is the flight to Illinois?

    An average nonstop flight from Kentucky to Illinois takes 5h 39m, covering a distance of 360 miles. The shortest route is Cincinnati (CVG) to Chicago Midway Airport (MDW) with an average flight time of 1h 05m.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (93% of total searches to Illinois). The next most popular destinations are St. Louis (5%) and Moline (1%). Searches for flights to Dubuque (0%) are also popular.

Top 5 airlines serving from Kentucky to Illinois

Need help choosing which airline to fly with from Kentucky to Illinois? 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
7.1Food
7.6Entertainment
8.6Crew
8.0Comfort
8.2Boarding
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.

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

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.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything was on time, we arrived early, everything worked well.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

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 Kentucky to Illinois

Recent round-trip flight deals

5/29Thu
nonstopFrontier
1h 58mBNA-ORD
6/1Sun
nonstopFrontier
1h 42mORD-BNA
$79
5/16Fri
nonstopSpirit Airlines
1h 57mBNA-ORD
5/19Mon
nonstopSpirit Airlines
1h 32mORD-BNA
$80
7/4Fri
nonstopAmerican Airlines
1h 50mBNA-ORD
7/6Sun
nonstopAmerican Airlines
1h 27mORD-BNA
$145
5/29Thu
nonstopSouthwest
1h 35mBNA-MDW
6/5Thu
nonstopSouthwest
1h 25mMDW-BNA
$145
5/29Thu
nonstopAmerican Airlines
1h 53mBNA-ORD
6/2Mon
nonstopAmerican Airlines
1h 39mORD-BNA
$146
6/18Wed
nonstopSouthwest
1h 40mBNA-MDW
6/22Sun
nonstopSouthwest
1h 25mMDW-BNA
$152
6/26Thu
1 stopDelta
6h 24mBNA-MDW
6/30Mon
1 stopDelta
3h 39mMDW-BNA
$177
6/1Sun
1 stopDelta
4h 13mBNA-ORD
6/4Wed
1 stopDelta
6h 07mORD-BNA
$177
5/30Fri
nonstopUnited Airlines
1h 57mTYS-ORD
6/1Sun
nonstopUnited Airlines
1h 45mORD-TYS
$189
7/10Thu
nonstopUnited Airlines
1h 43mLEX-ORD
7/17Thu
nonstopUnited Airlines
1h 31mORD-LEX
$194

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Recent one-way flight deals

5/29Thu
nonstopFrontier
1h 58mBNA-ORD
$38
5/19Mon
nonstopSpirit Airlines
1h 57mBNA-ORD
$39
6/29Sun
nonstopUnited Airlines
1h 58mBNA-ORD
$73
5/29Thu
nonstopSouthwest
1h 35mBNA-MDW
$73
8/5Tue
1 stopSouthwest
3h 15mBNA-MDW
$78
9/24Wed
nonstopUnited Airlines
1h 53mBNA-ORD
$80
5/30Fri
1 stopDelta
6h 26mBNA-MDW
$89
6/1Sun
1 stopDelta
4h 13mBNA-ORD
$89
5/30Fri
nonstopAmerican Airlines
1h 36mSDF-ORD
$90
5/31Sat
1 stopAmerican Airlines
7h 17mBNA-STL
$95

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Last minute flights from Kentucky to Illinois

Last minute flight, train and bus deals

5/5Mon
multi-stopFrontier
14h 05mBNA-STL
5/10Sat
multi-stopFrontier
22h 37mSTL-BNA
$181
5/5Mon
multi-stopFrontier
14h 05mBNA-STL
5/8Thu
multi-stopFrontier
15h 24mSTL-BNA
$188
5/3Sat
nonstopAmerican Airlines
2h 07mTYS-ORD
5/5Mon
nonstopAmerican Airlines
1h 43mORD-TYS
$264
5/3Sat
multi-stopAmerican Airlines
6h 45mTYS-ORD
5/5Mon
nonstopAmerican Airlines
1h 43mORD-TYS
$274
5/3Sat
multi-stopDelta
7h 20mLEX-ORD
5/4Sun
multi-stopDelta
3h 29mORD-LEX
$299
5/2Fri
multi-stopDelta
5h 47mTYS-MDW
5/5Mon
multi-stopDelta
6h 44mMDW-TYS
$314
5/3Sat
multi-stopUnited Airlines
16h 32mTYS-ORD
5/4Sun
multi-stopUnited Airlines
7h 21mORD-TYS
$414
5/4Sun
nonstopSouthwest
1h 35mBNA-MDW
5/27Tue
nonstopSouthwest
1h 30mMDW-BNA
$426
5/2Fri
multi-stopUnited Airlines
22h 26mSDF-ORD
5/3Sat
nonstopUnited Airlines
1h 35mORD-SDF
$429
5/4Sun
multi-stopSouthwest
4h 25mBNA-MDW
5/21Wed
nonstopSouthwest
1h 30mMDW-BNA
$436

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Everything you need to know for your flight to Illinois

Cabin class types available on flights to Kentucky

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

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