$59 Find Cheap Flights from Chicago to Kentucky - Compare and Save

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 8/13. 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.
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Cheap Flights from Chicago to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisvillenonstop$216
Lexington
Lexingtonnonstop$237
Nashville
Nashville1 stop$199
Louisville
Louisvillenonstop$216
Lexington
Lexingtonnonstop$237
Nashville
Nashville1 stop$199

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

Thu, Sep 10 - Tue, Sep 15
American Airlines Logo
6:30 pm - 9:04 pm
ORD
-
CVG
1h 34mnonstop
American Airlines Logo
11:58 am - 12:39 pm
CVG
-
ORD
1h 41mnonstop
$156American Airlines
Sat, Sep 12 - Mon, Sep 14
Southwest Logo
8:00 am - 10:25 am
MDW
-
CVG
1h 25mnonstop
Southwest Logo
7:00 pm - 7:10 pm
CVG
-
MDW
1h 10mnonstop
$157Southwest
Sat, Sep 5 - Sat, Sep 12
United Airlines Logo
12:50 pm - 3:21 pm
ORD
-
CVG
1h 31mnonstop
United Airlines Logo
7:00 am - 7:38 am
CVG
-
ORD
1h 38mnonstop
$157United Airlines
Thu, Oct 8 - Mon, Oct 12
United Airlines Logo
8:40 am - 11:11 am
ORD
-
CVG
1h 31mnonstop
United Airlines Logo
7:00 am - 7:34 am
CVG
-
ORD
1h 34mnonstop
$157United Airlines
Thu, Nov 5 - Mon, Nov 9
American Airlines Logo
10:15 pm - 12:39 am
ORD
-
CVG
1h 24mnonstop
American Airlines Logo
9:16 pm - 10:00 pm
CVG
-
ORD
1h 44mnonstop
$157American Airlines
Mon, Sep 7 - Mon, Sep 14
Southwest Logo
8:05 am - 10:25 am
MDW
-
CVG
1h 20mnonstop
Southwest Logo
7:00 pm - 7:10 pm
CVG
-
MDW
1h 10mnonstop
$157Southwest
Fri, Oct 9 - Mon, Oct 12
Allegiant Air Logo
12:26 pm - 2:51 pm
MDW
-
TYS
1h 25mnonstop
Allegiant Air Logo
12:04 pm - 12:36 pm
TYS
-
MDW
1h 32mnonstop
$159Allegiant Air
Thu, Aug 13 - Sun, Aug 16
Allegiant Air Logo
2:49 pm - 5:19 pm
MDW
-
TYS
1h 30mnonstop
Allegiant Air Logo
1:23 pm - 1:59 pm
TYS
-
MDW
1h 36mnonstop
$162Allegiant Air
Thu, Aug 20 - Tue, Aug 25
Delta Logo
9:24 am - 3:28 pm
MDW
-
CVG
5h 04m
1 stop
Delta Logo
2:23 pm - 6:33 pm
CVG
-
MDW
5h 10m
1 stop
$177Delta
Wed, Aug 19 - Sat, Aug 22
Delta Logo
1:25 pm - 6:04 pm
MDW
-
CVG
3h 39m
1 stop
Delta Logo
8:14 am - 12:39 pm
CVG
-
MDW
5h 25m
1 stop
$177Delta
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?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Kentucky departing in September.

Flight prices are below average for this route right now.

Flights to Kentucky from Chicago usually cost between $251 and $315 in September.
The lowest price found in the past 5 days was $216 on American Airlines (Sep 10-Sep 17).

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 5 days was to Owensboro, at $163 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Louisville (SDF), and the cheapest round-trip airline ticket found on this route in the last 5 days was $256.

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

The average price for all round-trip flights from Chicago to Kentucky depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Kentucky is generally in the morning, when round-trip flights cost $354 on average. Morning departures are around 28% cheaper than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the evening, which is peak travel time and where the average cost of a ticket is $489.

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 $388, 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 December, when tickets cost $247 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $485 and $465 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 Friday, and avoid Mondays 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 55% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low season

January

Cheapest flight

$59
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Chicago Midway Airport to Knoxville

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.

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 4228 reviews
7.0Food
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

I’ve flown Contour on 4 different flights in the last couple weeks and every one of the flights were significantly delayed. Like over 2 hours delayed. 3 of the 4 were due to maintenance and one was weather, which is beyond their control. If this continues, I will not fly them anymore. It makes me concerned that they don’t have great maintenance practices. The planes are very old and worn out and the interiors need improvement. I do like the amount of space you have between seats for legroom. They also started charging for bags recently, which I think the did when they partnered up with American Airlines as a codeshare partner. American is also a disaster of an airline so I wish they had some agreement with Delta. I am glad they offer a major airline parternership though. That is certainly giving people more opportunities. I won’t fly Contour unless they have a direct flight to where I am going. If I have to connect then I am going to take Delta. The bus at the DFW airport to get on and off the aircraft is a pain and adds so much extra time to your travel experience. I hope this is temporary while they are building a new terminal, but I don’t know.

Short flight so no entertainment and none expected or appropriate. Everyone I dealt with was professional and helpful. A good experience.

Love it. No Frills but better than Spirit No Frills. It's like a simple luxury private plane especially if you've got five or six people on it because then you probably got your own section of the plane.

All the staff were amazing! The flight was quick, everything went smoothly, I have nothing but good things to say about this flight. Thank you Contour!

It was easy, efficient from start to finish. The flight attendant was amazing. Smooth ride. It was just perfect.

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.

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

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.

It’s the only flight connecting Marion to Chicago, I do appreciate that it was available!

The boarding procedure is as easy and the crew very friendly.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The gate got changed several times and the flight was delayed over an hour. Awful experience

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

No Snacks or Entertainment. The flight was short, snacks should still be given.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

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.