$53 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 12/31. 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
Louisvillenonstop$133
Lexington
Lexingtonnonstop$189
Owensboro
Owensborononstop$104
Paducah
Paducahnonstop$211
Nashville
Nashvillenonstop$133
Louisville
Louisvillenonstop$133
Lexington
Lexingtonnonstop$189
Owensboro
Owensborononstop$104
Paducah
Paducahnonstop$211
Nashville
Nashvillenonstop$133

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

Mon, Dec 29 - Fri, Jan 2
Contour Logo
10:55 am - 12:25 pm
ORD
-
OWB
1h 30mnonstop
Contour Logo
3:10 pm - 4:45 pm
OWB
-
ORD
1h 35mnonstop
$104Contour
Tue, Dec 30 - Sat, Jan 3
Contour Logo
9:40 am - 11:10 am
ORD
-
OWB
1h 30mnonstop
Contour Logo
8:40 am - 10:15 am
OWB
-
ORD
1h 35mnonstop
$105Contour
Tue, Jan 13 - Tue, Jan 20
United Airlines Logo
7:50 pm - 9:42 pm
ORD
-
BNA
1h 52mnonstop
United Airlines Logo
10:55 am - 12:59 pm
BNA
-
ORD
2h 04mnonstop
$133United Airlines
Tue, Jan 6 - Tue, Jan 6
United Airlines Logo
10:45 am - 1:24 pm
ORD
-
SDF
1h 39mnonstop
United Airlines Logo
6:12 pm - 6:55 pm
SDF
-
ORD
1h 43mnonstop
$133United Airlines
Tue, Jan 13 - Tue, Jan 20
Multiple Airlines Logo
10:48 am - 5:48 pm
ORD
-
CVG
30h 00m1 stop
Multiple Airlines Logo
9:00 am - 10:04 pm
CVG
-
ORD
14h 04m1 stop
$134Multiple Airlines
Fri, Feb 20 - Sun, Feb 22
Frontier Logo
7:15 am - 7:45 pm
ORD
-
CVG
11h 30m1 stop
Frontier Logo
6:05 am - 9:40 pm
CVG
-
ORD
16h 35m1 stop
$135Frontier
Wed, Jan 21 - Mon, Jan 26
Multiple Airlines Logo
9:23 am - 3:12 pm
ORD
-
CVG
28h 49m1 stop
Multiple Airlines Logo
9:00 am - 9:43 am
CVG
-
ORD
25h 43m1 stop
$138Multiple Airlines
Thu, Jan 22 - Sat, Jan 24
Frontier Logo
11:51 am - 11:26 pm
ORD
-
CVG
10h 35m1 stop
Frontier Logo
10:00 am - 4:35 pm
CVG
-
ORD
7h 35m1 stop
$145Frontier
Mon, Jan 12 - Tue, Jan 13
American Airlines Logo
10:01 am - 12:32 pm
ORD
-
SDF
1h 31mnonstop
American Airlines Logo
7:13 pm - 8:05 pm
SDF
-
ORD
1h 52mnonstop
$152American Airlines
Thu, Jan 29 - Sun, Feb 1
American Airlines Logo
10:07 am - 12:46 pm
ORD
-
TYS
1h 39mnonstop
American Airlines Logo
7:54 am - 9:02 am
TYS
-
ORD
2h 08mnonstop
$189American 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.

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 $89 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 $97.

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 $228, 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 August, when tickets cost $186 (return) on average. On the other hand, the most expensive months are March and May, when the average cost of round-trip tickets is $423 and $367 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 Monday is the most expensive. Flying from Kentucky back to Chicago O'Hare Airport, the best deals are generally found on Thursday, 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 63% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$55
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 14% 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.

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

    The cheapest time of day to fly to Kentucky is generally at night, when round-trip flights cost $275 on average. Morning departures are around 3% 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 $305.

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 43 reviews
6.1Entertainment
7.6Boarding
7.9Crew
6.9Food
7.3Comfort
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.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

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.

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

Information on your arrival and departure airports