$77 Find Cheap Flights from Chicago O'Hare Airport to Kentucky - Compare and Save

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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 5 days
Louisville
Louisvillenonstop$197
Lexington
Lexingtonnonstop$279
Paducah
Paducahnonstop$194
Owensboro
Owensborononstop$162
Nashville
Nashville1 stop$225
Louisville
Louisvillenonstop$197
Lexington
Lexingtonnonstop$279
Paducah
Paducahnonstop$194
Owensboro
Owensborononstop$162
Nashville
Nashville1 stop$225
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?

Flight prices are below average for this route right now.

Flights to Kentucky from Chicago O'Hare Intl Airport usually cost between $280 and $486 in October.
The lowest price found in the past 5 days was $197 on United Airlines (Oct 24-Oct 31).

What is the cheapest Chicago O'Hare Intl Airport to Kentucky flight route?

The cheapest ticket to Kentucky from Chicago O'Hare Intl Airport found in the last 5 days was to Owensboro, at $129 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 $235.

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

The cheapest time of day to fly to Kentucky is generally in the morning, when round-trip flights cost $373 on average. Morning departures are around 23% 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 $487.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Kentucky?

No, with an average price for the route of $334, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Chicago O'Hare Intl Airport to Kentucky is December, when tickets cost $262 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $452 and $449 respectively.

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

For Chicago O'Hare Airport to Kentucky, Thursday 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 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 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 48% 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

December

Cheapest flight

$77
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 12% 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

 
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.
7.5
ContourOverall score based on 43 reviews
6.8Food
7.3Comfort
6.1Entertainment
7.5Boarding
7.8Crew
Airline reviews

You could have NOT left me and my family high and dry by not completing the reservation changes because they no longer have the contract from Phoenix AZ to Moab Utah. There wasn't even a ticket agent for Contour in Phoenix to talk to. Cost my an additional $1600. to rent a vehicle to get my family to Utah. Now I'm left with trying to have someone make it right financially. I'm not optimistic..........

2.0 MediocreBarbra, Aug 2026
Read more Contour reviews

You could have NOT left me and my family high and dry by not completing the reservation changes because they no longer have the contract from Phoenix AZ to Moab Utah. There wasn't even a ticket agent for Contour in Phoenix to talk to. Cost my an additional $1600. to rent a vehicle to get my family to Utah. Now I'm left with trying to have someone make it right financially. I'm not optimistic..........

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.

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.

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

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.

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

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

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.

More options for your flight from O'Hare Intl to Kentucky

Complete your trip to Kentucky with a hotel stay or car rental