$43 Find Cheap Flights from Chicago to Kentucky - Compare and Save

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Cheap Flights from Chicago to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Cincinnati
1h 10mNonstop
from $121per person
Owensboro
1h 30mNonstop
from $162per person
Paducah
1h 27mNonstop
from $194per person
Louisville
1h 10mNonstop
from $197per person
Nashville
1h 25mNonstop
from $225per person
Knoxville
1h 25mNonstop
from $248per person
Lexington
1h 31mNonstop
from $279per person
Blountville
1h 49mNonstop
from $279per person
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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.

How much is a round-trip flight from Chicago to Kentucky?

Flight prices are below average for this route right now.

Flights to Kentucky from Chicago usually cost between $337 and $531 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 to Kentucky flight route?

The cheapest ticket to Kentucky from Chicago 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 to Kentucky?

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 $273 on average.

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

The cheapest month for flights from Chicago to Kentucky is December, when tickets cost $264 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $485 and $470 respectively.

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

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

How far in advance should I book a flight from Chicago to Kentucky?

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 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

January

Cheapest flight

$43
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from Chicago Midway Airport to Knoxville

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.

Reviews of the top 4 airlines serving from Chicago to Kentucky

 
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 4189 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

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

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

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 Chicago to Kentucky

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