$28 Find Cheap Flights from Kentucky to Illinois

1 adult
1 adult, Economy

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

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 seasonJuly
Cheapest flight$28
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 7% 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 $228.

  • 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 $486. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $703 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 $513 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 evening, which is peak travel time and where the average cost of a ticket is $874.

  • 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 $114 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 $114.

  • 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 6h 10m, 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 (92% of total searches to Illinois). The next most popular destinations are St. Louis (7%) and Moline (1%). Searches for flights to Dubuque (0%) are also popular.

Reviews of the 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 4247 reviews
7.6Entertainment
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
Airline reviews

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

6.0 GoodAnonymous, Jul 2025BDL - MDW
Read more Southwest reviews

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

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.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

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 flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

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

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.

Book cheap flights from Kentucky to Illinois

Recent round-trip flight deals

8/4Mon
nonstopAllegiant Air
1h 33mTYS-MDW
8/8Fri
nonstopAllegiant Air
1h 26mMDW-TYS
$48
9/19Fri
nonstopAllegiant Air
1h 36mTYS-MDW
9/22Mon
nonstopAllegiant Air
1h 31mMDW-TYS
$50
8/8Fri
nonstopSpirit Airlines
2h 03mBNA-ORD
8/11Mon
nonstopSpirit Airlines
1h 29mORD-BNA
$58
8/1Fri
nonstopSpirit Airlines
2h 03mBNA-ORD
8/11Mon
nonstopSpirit Airlines
1h 29mORD-BNA
$60
8/7Thu
nonstopSouthwest
1h 20mSDF-MDW
8/14Thu
nonstopSouthwest
1h 10mMDW-SDF
$91
8/8Fri
nonstopSouthwest
1h 35mBNA-MDW
8/15Fri
nonstopSouthwest
1h 25mMDW-BNA
$91
8/9Sat
nonstopUnited Airlines
1h 37mSDF-ORD
8/16Sat
nonstopUnited Airlines
1h 32mORD-SDF
$97
8/6Wed
nonstopAmerican Airlines
1h 46mSDF-ORD
8/16Sat
nonstopAmerican Airlines
1h 25mORD-SDF
$101
8/6Wed
nonstopAmerican Airlines
1h 50mBNA-ORD
8/13Wed
nonstopAmerican Airlines
1h 45mORD-BNA
$101
8/6Wed
nonstopUnited Airlines
1h 29mCVG-ORD
8/13Wed
nonstopUnited Airlines
1h 26mORD-CVG
$101

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/11Mon
nonstopSpirit Airlines
2h 03mBNA-ORD
$28
8/1Fri
nonstopSpirit Airlines
2h 03mBNA-ORD
$29
7/25Fri
nonstopFrontier
2h 04mBNA-ORD
$39
8/3Sun
nonstopFrontier
2h 04mBNA-ORD
$45
8/9Sat
nonstopSouthwest
1h 15mSDF-MDW
$46
8/5Tue
nonstopSouthwest
1h 35mBNA-MDW
$46
8/12Tue
nonstopAmerican Airlines
1h 46mSDF-ORD
$49
8/27Wed
nonstopUnited Airlines
1h 54mBNA-ORD
$49
8/9Sat
nonstopAmerican Airlines
1h 42mSDF-ORD
$51
10/14Tue
nonstopUnited Airlines
2h 01mBNA-ORD
$51

Search by stops

Search by airline

Search by price

Last minute flights from Kentucky to Illinois

Last minute flight, train and bus deals

7/14Mon
nonstopFrontier
2h 04mBNA-ORD
7/18Fri
nonstopFrontier
1h 39mORD-BNA
$130
7/14Mon
nonstopFrontier
2h 04mBNA-ORD
7/18Fri
nonstopFrontier
1h 39mORD-BNA
$135
7/14Mon
nonstop
2h 03mBNA-ORD
7/18Fri
nonstop
1h 39mORD-BNA
$141
7/15Tue
multi-stop
9h 13mBNA-ORD
7/18Fri
nonstop
1h 39mORD-BNA
$149
7/15Tue
nonstopAmerican Airlines
1h 38mLEX-ORD
7/19Sat
nonstopAmerican Airlines
1h 27mORD-LEX
$252
7/15Tue
multi-stopAmerican Airlines
5h 09mLEX-ORD
7/19Sat
nonstopAmerican Airlines
1h 27mORD-LEX
$262
7/16Wed
nonstopSouthwest
1h 35mBNA-MDW
7/19Sat
nonstopSouthwest
1h 30mMDW-BNA
$337
7/16Wed
nonstopSouthwest
1h 35mBNA-MDW
7/19Sat
multi-stopSouthwest
3h 05mMDW-BNA
$343
7/16Wed
nonstopUnited Airlines
1h 57mTYS-ORD
7/20Sun
nonstopUnited Airlines
1h 45mORD-TYS
$364
7/17Thu
nonstopUnited Airlines
1h 57mTYS-ORD
7/27Sun
nonstopUnited Airlines
1h 45mORD-TYS
$383

Search by stops

Search by airline

Search by price

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.

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