$77 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Kentucky departing on 7/14. 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, 0 bags

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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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Cheap Flights from O'Hare Intl to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisvillenonstop$177
Lexington
Lexingtonnonstop$249
Paducah
Paducahnonstop$194
Owensboro
Owensborononstop$159
Nashville
Nashville1 stop$220
Louisville
Louisvillenonstop$177
Lexington
Lexingtonnonstop$249
Paducah
Paducahnonstop$194
Owensboro
Owensborononstop$159
Nashville
Nashville1 stop$220

Book Cheap O'Hare Intl 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 O'Hare Intl 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 O'Hare Intl to Kentucky

Tue, Jul 7 - Wed, Jul 8
American Airlines Logo
10:00 pm - 12:30 am
ORD
-
CVG
1h 30mnonstop
American Airlines Logo
6:00 am - 6:32 am
CVG
-
ORD
1h 32mnonstop
$157American Airlines
Sat, Jul 11 - Sat, Jul 18
Contour Logo
11:20 am - 12:55 pm
ORD
-
OWB
1h 35mnonstop
Contour Logo
9:00 am - 10:40 am
OWB
-
ORD
1h 40mnonstop
$159Contour
Tue, Aug 11 - Sat, Aug 15
Contour Logo
11:20 am - 12:55 pm
ORD
-
OWB
1h 35mnonstop
Contour Logo
9:00 am - 10:40 am
OWB
-
ORD
1h 40mnonstop
$160Contour
Wed, Aug 19 - Sat, Aug 22
United Airlines Logo
6:50 am - 9:16 am
ORD
-
CVG
1h 26mnonstop
United Airlines Logo
2:05 pm - 2:39 pm
CVG
-
ORD
1h 34mnonstop
$176United Airlines
Tue, Aug 18 - Tue, Aug 18
United Airlines Logo
7:00 am - 9:42 am
ORD
-
SDF
1h 42mnonstop
United Airlines Logo
5:45 pm - 6:36 pm
SDF
-
ORD
1h 51mnonstop
$177United Airlines
Tue, Jul 7 - Wed, Jul 8
Delta Logo
2:07 pm - 7:54 pm
ORD
-
CVG
4h 47m
1 stop
Delta Logo
11:03 am - 4:23 pm
CVG
-
ORD
6h 20m
1 stop
$177Delta
Mon, Aug 17 - Tue, Aug 18
Delta Logo
5:20 pm - 10:40 pm
ORD
-
CVG
4h 20m
1 stop
Delta Logo
10:53 am - 4:17 pm
CVG
-
ORD
6h 24m
1 stop
$196Delta
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
8:59 pm - 11:29 pm
ORD
-
CVG
1h 30mnonstop
American Airlines Logo
12:34 pm - 1:14 pm
CVG
-
ORD
1h 40mnonstop
$197American Airlines
Thu, Aug 6 - Mon, Aug 10
Frontier Logo
1:50 pm - 11:48 am
ORD
-
CVG
20h 58m
1 stop
Frontier Logo
12:53 pm - 8:02 am
CVG
-
ORD
20h 09m
1 stop
$201Frontier
Thu, Aug 6 - Mon, Aug 10
Frontier Logo
1:50 pm - 11:48 am
ORD
-
CVG
20h 58m
1 stop
Frontier Logo
12:53 pm - 8:02 am
CVG
-
ORD
20h 09m
1 stop
$207Frontier
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Kentucky flights

Get data-powered insights and trends into flights from O'Hare Intl 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Kentucky departing in August.

What is the cheapest Chicago O'Hare Intl Airport 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 O'Hare Intl Airport found in the last 5 days was to Owensboro, at $154 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 $275.

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

The average price for all round-trip flights from Chicago O'Hare Intl Airport 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 $333 on average. Morning departures are around 25% 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 $444.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport 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 $344, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Kentucky?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Kentucky is July, when tickets cost $69 (return) on average. On the other hand, the most expensive months are May and June, when the average cost of round-trip tickets is $206 and $176 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Kentucky?

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

For Chicago O'Hare Airport to Kentucky, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Kentucky back to Chicago O'Hare Airport, the best deals are generally found on Friday, with Sunday being the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Kentucky, you should book around 4 weeks before departure, which saves you about 59% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$77
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Chicago to Owensboro

FAQs - booking Kentucky flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Kentucky.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 3 airlines serving from O'Hare Intl 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 O'Hare Intl 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.
7.7
ContourOverall score based on 42 reviews
6.2Entertainment
6.9Food
7.4Comfort
8.0Crew
7.7Boarding
Airline reviews

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.

6.0 GoodLane, Jun 2026
DFW - TUP
Read more Contour reviews

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.

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.

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.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Everything you need to know for your flight from O'Hare Intl to Kentucky

Information on your arrival and departure airports