$61 Find Cheap Flights from Chicago O'Hare Airport 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 O'Hare Intl to Kentucky departing on 5/15. 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

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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Cheap Flights from O'Hare Intl to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisville1 stop$210
Lexington
Lexington1 stop$236
Owensboro
Owensborononstop$124
Paducah
Paducahnonstop$194
Nashville
Nashville1 stop$218
Louisville
Louisville1 stop$210
Lexington
Lexington1 stop$236
Owensboro
Owensborononstop$124
Paducah
Paducahnonstop$194
Nashville
Nashville1 stop$218

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

Wed, May 27 - Sat, May 30
Contour Logo
11:20 am - 12:55 pm
ORD
-
OWB
1h 35mnonstop
Contour Logo
9:00 am - 10:40 am
OWB
-
ORD
1h 40mnonstop
$124Contour
Tue, May 12 - Sat, May 16
Contour Logo
11:20 am - 12:55 pm
ORD
-
OWB
1h 35mnonstop
Contour Logo
2:35 pm - 4:15 pm
OWB
-
ORD
1h 40mnonstop
$125Contour
Thu, May 21 - Sat, May 23
American Airlines Logo
7:30 pm - 10:02 pm
ORD
-
CVG
1h 32mnonstop
American Airlines Logo
12:06 pm - 12:37 pm
CVG
-
ORD
1h 31mnonstop
$191American Airlines
Thu, May 21 - Mon, May 25
American Airlines Logo
11:03 am - 1:37 pm
ORD
-
CVG
1h 34mnonstop
American Airlines Logo
12:06 pm - 12:37 pm
CVG
-
ORD
1h 31mnonstop
$192American Airlines
Sat, May 23 - Sat, May 30
Frontier Logo
6:55 am - 11:04 am
ORD
-
CVG
27h 09m
1 stop
Frontier Logo
12:46 pm - 7:41 pm
CVG
-
ORD
7h 55m
1 stop
$193Frontier
Wed, May 13 - Sun, May 17
United Airlines Logo
12:07 pm - 1:35 pm
ORD
-
PAH
1h 28mnonstop
United Airlines Logo
5:00 am - 6:41 am
PAH
-
ORD
1h 41mnonstop
$194United Airlines
Wed, May 20 - Sat, May 23
Delta Logo
9:25 am - 3:14 pm
ORD
-
CVG
4h 49m
1 stop
Delta Logo
5:44 pm - 9:46 pm
CVG
-
ORD
5h 02m
1 stop
$194Delta
Fri, Jun 19 - Tue, Jun 23
Frontier Logo
6:55 am - 11:47 am
ORD
-
CVG
27h 52m
1 stop
Frontier Logo
12:24 pm - 7:53 pm
CVG
-
ORD
8h 29m
1 stop
$196Frontier
Wed, May 27 - Mon, Jun 1
Delta Logo
6:24 am - 1:27 pm
ORD
-
CVG
6h 03m
2 stops
Delta Logo
2:07 pm - 6:05 pm
CVG
-
ORD
4h 58m
1 stop
$199Delta
Fri, May 15 - Mon, May 18
United Airlines Logo
12:07 pm - 1:35 pm
ORD
-
PAH
1h 28mnonstop
United Airlines Logo
5:00 am - 6:35 am
PAH
-
ORD
1h 35mnonstop
$234United Airlines
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 May.

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 72 hours was to Owensboro, at $104 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 72 hours was $257.

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 $306 on average. Morning departures are around 15% cheaper than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $383.

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 $312, 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 November and May, when the average cost of round-trip tickets is $174 and $148 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 Monday 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 60% 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$61
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 10% 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.
7.6
ContourOverall score based on 42 reviews
7.3Comfort
7.9Crew
6.1Entertainment
7.6Boarding
6.8Food
Airline reviews

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

10.0 ExcellentAnonymous, Nov 2025
TSM - DEN
Read more Contour reviews

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.

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.

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.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

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.

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

American continues to decline in their customer service and its beyond disappointing.

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.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

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

Information on your arrival and departure airports