$39 Find Cheap Flights from Chicago to Kentucky

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Kentucky departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kentucky, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kentucky, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Chicago to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisvillenonstop$97
Lexington
Lexingtonnonstop$189
Nashville
Nashvillenonstop$77
Louisville
Louisvillenonstop$97
Lexington
Lexingtonnonstop$189
Nashville
Nashvillenonstop$77

Book Cheap Chicago to Kentucky Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Kentucky that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Kentucky

Fri, Nov 7 - Mon, Nov 10
Spirit Airlines Logo
4:01 pm - 5:41 pmORD-BNA
1h 40mnonstop
Spirit Airlines Logo
6:46 pm - 8:31 pmBNA-ORD
1h 45mnonstop
$77Spirit Airlines
Find Deal
Sun, Oct 12 - Mon, Oct 13
Multiple Airlines Logo
1:26 pm - 3:10 pmORD-BNA
1h 44mnonstop
Multiple Airlines Logo
9:59 pm - 11:44 pmBNA-ORD
1h 45mnonstop
$78Multiple Airlines
Find Deal
Thu, Nov 13 - Sun, Nov 16
Frontier Logo
6:06 pm - 7:54 pmORD-BNA
1h 48mnonstop
Frontier Logo
8:53 pm - 10:41 pmBNA-ORD
1h 48mnonstop
$83Frontier
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Thu, Oct 9 - Mon, Oct 13
Frontier Logo
12:53 pm - 2:29 pmORD-BNA
1h 36mnonstop
Frontier Logo
9:59 pm - 11:44 pmBNA-ORD
1h 45mnonstop
$86Frontier
Find Deal
Thu, Oct 9 - Wed, Oct 15
American Airlines Logo
8:28 pm - 11:03 pmORD-SDF
1h 35mnonstop
American Airlines Logo
5:53 pm - 6:29 pmSDF-ORD
1h 36mnonstop
$97American Airlines
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Tue, Oct 14 - Wed, Oct 15
Southwest Logo
3:10 pm - 4:45 pmORD-BNA
1h 35mnonstop
Southwest Logo
10:55 am - 12:45 pmBNA-ORD
1h 50mnonstop
$97Southwest
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Mon, Oct 13 - Thu, Oct 16
Southwest Logo
9:30 pm - 10:55 pmMDW-BNA
1h 25mnonstop
Southwest Logo
7:30 am - 9:05 amBNA-MDW
1h 35mnonstop
$97Southwest
Find Deal
Thu, Oct 23 - Mon, Oct 27
American Airlines Logo
7:00 am - 8:32 amORD-BNA
1h 32mnonstop
American Airlines Logo
5:35 am - 7:30 amBNA-ORD
1h 55mnonstop
$98American Airlines
Find Deal
Sat, Oct 11 - Mon, Oct 13
United Airlines Logo
10:50 am - 1:21 pmORD-SDF
1h 31mnonstop
United Airlines Logo
7:00 am - 7:38 amSDF-ORD
1h 38mnonstop
$114United Airlines
Find Deal
Sun, Oct 19 - Sat, Oct 25
United Airlines Logo
7:15 am - 8:55 amORD-BNA
1h 40mnonstop
United Airlines Logo
6:00 am - 8:01 amBNA-ORD
2h 01mnonstop
$127United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Kentucky flights

Get data-powered insights and trends into flights from Chicago to Kentucky to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Chicago to Kentucky?

What is the cheapest Chicago to Kentucky flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Kentucky from Chicago found in the last 72 hours was to Louisville, at $97 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Lexington (LEX), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $189.

Can I save money by flying with a layover from Chicago to Kentucky?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $230, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Kentucky?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Kentucky, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Kentucky is August, when tickets cost $157 (return) on average. On the other hand, the most expensive months are February and June, when the average cost of round-trip tickets is $495 and $436 respectively.

What’s the cheapest day of the week to fly from Chicago to Kentucky?

The average price of all round-trip flights from Chicago to Kentucky clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Kentucky on a Saturday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Sundays for better deals.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Kentucky, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Kentucky, you should book around 4 weeks before departure, which saves you about 62% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$39
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago O'Hare Airport to Nashville

FAQs - booking Kentucky flights

  • How does KAYAK find such low prices on flights from Chicago 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 Chicago to Kentucky.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 Chicago 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 Chicago 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 Chicago 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 Chicago to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    The cheapest time of day to fly to Kentucky is generally in the afternoon, when round-trip flights cost $285 on average. Morning departures are around 7% 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 $319.

Reviews of the top 4 airlines serving from Chicago to Kentucky

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kentucky. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago 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 4242 reviews
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

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

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.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

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

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.

We had a great experience on both of our flights! Crew was great…..the ride was smooth…and checking in was easy. We will definitely fly with them again.

This was my first time flying with Contour and the Greenbrier Valley Airport. It both were excellent and the price couldn’t be beat!

Not on time. Taxied around the airport for 30 MINUTES! The pilot never said a word. Ai

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!

Everything you need to know for your flight from Chicago to Kentucky

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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