$30 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 10/27. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Booking Insights
Flights Deals

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$97
Lexington
Lexingtonnonstop$188
Owensboro
Owensborononstop$127
Paducah
Paducah2 stops$355
Nashville
Nashvillenonstop$59
Louisville
Louisvillenonstop$97
Lexington
Lexingtonnonstop$188
Owensboro
Owensborononstop$127
Paducah
Paducah2 stops$355
Nashville
Nashvillenonstop$59

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, Nov 10 - Thu, Nov 13
Spirit Airlines Logo
4:01 pm - 5:41 pmORD-BNA
1h 40mnonstop
Spirit Airlines Logo
6:46 pm - 8:31 pmBNA-ORD
1h 45mnonstop
$59Spirit Airlines
Find Deal
Mon, Nov 10 - Thu, Nov 13
Spirit Airlines Logo
4:01 pm - 5:41 pmORD-BNA
1h 40mnonstop
Spirit Airlines Logo
6:46 pm - 8:31 pmBNA-ORD
1h 45mnonstop
$64Spirit Airlines
Find Deal
Thu, Oct 23 - Fri, Oct 24
Frontier Logo
1:52 pm - 3:35 pmORD-BNA
1h 43mnonstop
Frontier Logo
4:20 pm - 6:15 pmBNA-ORD
1h 55mnonstop
$74Frontier
Find Deal
Thu, Oct 30 - Mon, Nov 3
Frontier Logo
1:52 pm - 3:35 pmORD-BNA
1h 43mnonstop
Frontier Logo
4:20 pm - 6:15 pmBNA-ORD
1h 55mnonstop
$75Frontier
Find Deal
Sat, Aug 23 - Sat, Aug 23
United Airlines Logo
7:26 am - 10:00 amORD-SDF
1h 34mnonstop
United Airlines Logo
7:36 pm - 8:25 pmSDF-ORD
1h 49mnonstop
$97United Airlines
Find Deal
Wed, Sep 10 - Wed, Sep 17
United Airlines Logo
7:26 am - 10:02 amORD-SDF
1h 36mnonstop
United Airlines Logo
10:55 am - 11:33 amSDF-ORD
1h 38mnonstop
$113United Airlines
Find Deal
Sat, Aug 23 - Mon, Aug 25
American Airlines Logo
11:52 am - 2:19 pmORD-SDF
1h 27mnonstop
American Airlines Logo
2:42 pm - 3:24 pmSDF-ORD
1h 42mnonstop
$124American Airlines
Find Deal
Tue, Nov 11 - Sat, Nov 15
Contour Logo
10:10 am - 11:40 amORD-OWB
1h 30mnonstop
Contour Logo
7:15 am - 8:50 amOWB-ORD
1h 35mnonstop
$127Contour
Find Deal
Sat, Aug 30 - Sun, Aug 31
American Airlines Logo
3:17 pm - 5:43 pmORD-SDF
1h 26mnonstop
American Airlines Logo
2:42 pm - 3:24 pmSDF-ORD
1h 42mnonstop
$138American Airlines
Find Deal
Thu, Oct 2 - Mon, Oct 6
Contour Logo
4:30 pm - 6:00 pmORD-OWB
1h 30mnonstop
Contour Logo
7:30 am - 9:05 amOWB-ORD
1h 35mnonstop
$138Contour
Find Deal
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago O'Hare Intl Airport to Kentucky.

The cheapest ticket to Kentucky from Chicago O'Hare Intl Airport found in the last 72 hours was to Louisville, at $141 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 $141.

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 $415, 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 $226 (return) on average. On the other hand, the most expensive months are September and July, when the average cost of round-trip tickets is $478 and $468 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 61% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.


Good to know

Low seasonJanuary
Cheapest flight$30
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Chicago O'Hare Airport to Nashville

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 in the afternoon, when round-trip flights cost $291 on average. Morning departures are around 9% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the morning, which is peak travel time and where the average cost of a ticket is $321.

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.
7.4
United AirlinesOverall score based on 8896 reviews
8.1Crew
7.7Boarding
7.3Comfort
6.6Food
7.1Entertainment
Airline reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

10.0 ExcellentAnita, Jul 2025ORD - CMH
Read more United Airlines reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

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.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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.

Flight was cancelled, but they got him on an earlier delayed rescheduled one. Arrived Chicago 2 hours later than expected but long layover so it worked.

Crew very helpful, weather made the flight less than optimal.

Flight was fine. I just forgot how smaller planes have more dips and seats in high winds.

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

The flight was delayed and then less than 30 mins before boarding they cancelled the flight when clearly they had to have known earlier that they were going to have to cancel. There was only one person there available to talk to and all he could do was tell us to call reservations our self. Due to high call volume I waited 2 hours to even get rebooked on a flight to a different city where I would still have to drive 1 hr to my destination, only option for me. While waiting to talk to reservations people were getting emails with new flight info and the flights were days out and sone even a week out. . I did not get compensated in anyway after having spent all day at the airpot, not even a food voucher. Very disappointed, terrible experience.

Information regarding the delayed flight could have been better, and the Contour airlines app needs some serious updates. But overall, the crew was great and the flight was uneventful.

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

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.