$38 Find Cheap Flights from Kentucky to Illinois

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Low seasonJanuary
High seasonAugust
Cheapest flight$38
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 15% 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 $244.

  • 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 $487. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $717 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 $512 on average. Morning departures are around 41% 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 $901.

  • 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 $120 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 $120.

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

    The cheapest month for flights from Kentucky to Illinois is September, when tickets cost $117 (return) on average. On the other hand, the most expensive months are October and December, when the average cost of round-trip tickets is $216 and $160 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 7h 02m, 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 (94% 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 4 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 4278 reviews
8.6Crew
8.0Comfort
7.1Food
8.2Boarding
7.6Entertainment
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

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.

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 liked that the flight was nonstop from ORD to CIU for $200 round trip.

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!

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

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

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

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.

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.

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.

Book cheap flights from Kentucky to Illinois

Recent round-trip flight deals

8/7Thu
nonstopUnited Airlines
1h 37mSDF-ORD
8/11Mon
nonstopUnited Airlines
1h 34mORD-SDF
$77
8/7Thu
nonstopSouthwest
1h 20mSDF-MDW
8/11Mon
nonstopSouthwest
1h 20mMDW-SDF
$77
8/7Thu
nonstopSouthwest
1h 35mBNA-MDW
8/11Mon
nonstopSouthwest
1h 25mMDW-BNA
$77
7/21Mon
nonstopAllegiant Air
1h 33mTYS-MDW
7/25Fri
nonstopAllegiant Air
1h 26mMDW-TYS
$78
6/26Thu
nonstopAllegiant Air
1h 31mBNA-RFD
6/29Sun
nonstopAllegiant Air
1h 25mRFD-BNA
$78
9/19Fri
nonstopSpirit Airlines
1h 50mBNA-ORD
9/22Mon
nonstopSpirit Airlines
1h 35mORD-BNA
$78
7/11Fri
nonstopSpirit Airlines
2h 03mBNA-ORD
7/14Mon
nonstopSpirit Airlines
1h 29mORD-BNA
$88
11/11Tue
nonstopAmerican Airlines
1h 33mSDF-ORD
11/11Tue
nonstopAmerican Airlines
1h 30mORD-SDF
$91
8/7Thu
nonstopAmerican Airlines
1h 52mBNA-ORD
8/11Mon
nonstopAmerican Airlines
1h 36mORD-BNA
$91
9/15Mon
nonstopUnited Airlines
1h 53mBNA-ORD
9/18Thu
nonstopUnited Airlines
1h 40mORD-BNA
$93

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Recent one-way flight deals

7/18Fri
nonstopSpirit Airlines
2h 03mBNA-ORD
$38
8/4Mon
nonstopUnited Airlines
1h 42mSDF-ORD
$39
8/4Mon
nonstopSouthwest
1h 15mSDF-MDW
$39
8/4Mon
nonstopSouthwest
1h 35mBNA-MDW
$39
7/10Thu
nonstopAllegiant Air
1h 31mBNA-RFD
$39
7/3Thu
nonstopAllegiant Air
1h 31mBNA-RFD
$42
11/3Mon
nonstopAmerican Airlines
1h 39mSDF-ORD
$46
10/16Thu
nonstopAmerican Airlines
1h 49mBNA-ORD
$46
6/23Mon
nonstopFrontier
1h 49mBNA-ORD
$62
6/27Fri
1 stopFrontier
6h 35mCVG-MDW
$100

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Last minute flights from Kentucky to Illinois

Last minute flight, train and bus deals

6/19Thu
nonstopAllegiant Air
1h 31mBNA-RFD
6/22Sun
nonstopAllegiant Air
1h 25mRFD-BNA
$107
6/20Fri
nonstopFrontier
1h 49mBNA-ORD
6/23Mon
nonstopFrontier
1h 44mORD-BNA
$112
6/20Fri
nonstop
1h 49mBNA-ORD
6/23Mon
nonstop
1h 29mORD-BNA
$113
6/20Fri
nonstop
1h 49mBNA-ORD
6/23Mon
nonstop
1h 29mORD-BNA
$120
6/21Sat
nonstopAmerican Airlines
1h 35mLEX-ORD
6/22Sun
nonstopAmerican Airlines
1h 34mORD-LEX
$249
6/17Tue
nonstopAmerican Airlines
1h 35mLEX-ORD
6/23Mon
nonstopAmerican Airlines
1h 24mORD-LEX
$252
6/21Sat
nonstopSouthwest
1h 35mBNA-MDW
6/22Sun
nonstopSouthwest
1h 25mMDW-BNA
$337
6/21Sat
nonstopSouthwest
1h 35mBNA-MDW
6/22Sun
multi-stopSouthwest
4h 20mMDW-BNA
$347
6/19Thu
nonstopUnited Airlines
1h 51mLEX-ORD
6/23Mon
nonstopUnited Airlines
1h 39mORD-LEX
$451
6/20Fri
nonstopUnited Airlines
2h 04mTYS-ORD
6/23Mon
multi-stopUnited Airlines
12h 07mORD-TYS
$467

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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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