$61 Find Cheap Flights from Chicago 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 Chicago to Kentucky departing on 2/28. 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 Chicago to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisvillenonstop$177
Lexington
Lexingtonnonstop$189
Nashville
Nashvillenonstop$191
Louisville
Louisvillenonstop$177
Lexington
Lexingtonnonstop$189
Nashville
Nashvillenonstop$191

Book Cheap Chicago 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 Chicago 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 Chicago to Kentucky

Sat, Feb 21 - Mon, Feb 23
Frontier Logo
5:05 am - 11:33 pm
ORD
-
CVG
17h 28m
1 stop
Frontier Logo
1:07 pm - 10:51 am
CVG
-
ORD
22h 44m
1 stop
$138Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
5:05 am - 5:32 pm
ORD
-
CVG
11h 27m
1 stop
Frontier Logo
1:07 pm - 10:51 am
CVG
-
ORD
22h 44m
1 stop
$145Frontier
Tue, Feb 24 - Tue, Mar 3
United Airlines Logo
10:50 am - 1:17 pm
ORD
-
CVG
1h 27mnonstop
United Airlines Logo
4:15 pm - 4:50 pm
CVG
-
ORD
1h 35mnonstop
$157United Airlines
Tue, Feb 17 - Thu, Feb 19
United Airlines Logo
1:01 pm - 3:28 pm
ORD
-
CVG
1h 27mnonstop
United Airlines Logo
7:00 am - 7:32 am
CVG
-
ORD
1h 32mnonstop
$162United Airlines
Thu, Mar 5 - Tue, Mar 10
Southwest Logo
7:15 pm - 9:30 pm
MDW
-
CVG
1h 15mnonstop
Southwest Logo
7:35 pm - 7:45 pm
CVG
-
MDW
1h 10mnonstop
$164Southwest
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
5:30 pm - 7:40 pm
MDW
-
CVG
1h 10mnonstop
Southwest Logo
1:35 pm - 6:05 pm
CVG
-
MDW
5h 30m
1 stop
$167Southwest
Wed, Mar 25 - Sat, Mar 28
American Airlines Logo
8:50 pm - 11:20 pm
ORD
-
SDF
1h 30mnonstop
American Airlines Logo
7:30 am - 8:12 am
SDF
-
ORD
1h 42mnonstop
$184American Airlines
Thu, Feb 26 - Mon, Mar 2
American Airlines Logo
7:04 am - 9:28 am
ORD
-
LEX
1h 24mnonstop
American Airlines Logo
5:07 pm - 5:47 pm
LEX
-
ORD
1h 40mnonstop
$189American Airlines
Wed, Mar 4 - Thu, Mar 12
Multiple Airlines Logo
8:16 pm - 11:27 pm
ORD
-
TYS
26h 11m
1 stop
Multiple Airlines Logo
9:43 pm - 11:21 am
TYS
-
ORD
14h 38m
1 stop
$190Multiple Airlines
Tue, Feb 24 - Sat, Feb 28
Multiple Airlines Logo
6:10 am - 7:25 am
MDW
-
BNA
25h 15m
2 stops
Multiple Airlines Logo
6:15 am - 2:55 pm
BNA
-
MDW
8h 40m
1 stop
$193Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Kentucky flights

Get data-powered insights and trends into flights from Chicago to Kentucky to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago 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 found in the last 72 hours was to Owensboro, at $105 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 $143.

Can I save money by flying with a layover from Chicago 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $198 on average.

What is the cheapest month to fly from Chicago to Kentucky?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 to Kentucky is August, when tickets cost $157 (return) on average. On the other hand, the most expensive months are June and February, when the average cost of round-trip tickets is $454 and $359 respectively.

What’s the cheapest day of the week to fly from Chicago to Kentucky?

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

Your flight ticket price will generally be cheaper if you fly to Kentucky on a Saturday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Thursday, and avoid Sundays for better deals.

How far in advance should I book a flight from Chicago 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 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 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 17 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$61
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to Cincinnati

FAQs - booking Kentucky flights

  • How does KAYAK find such low prices on flights from Chicago 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 to Kentucky.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 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 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 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 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 8% 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 $315.

Reviews of the top 4 airlines serving from Chicago 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 Chicago 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.
8.0
SouthwestOverall score based on 4267 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

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.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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.

Everything you need to know for your flight from Chicago to Kentucky

Cabin class types available on flights to Kentucky

Cabin classes available on flights to Kentucky. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.