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Find cheap flights from Chicago Midway Airport to Kentucky from $47

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Kentucky departing on 6/3. 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
0 bags
sáb 6/15
sáb 6/22

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Best Kentucky Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Louisville
Louisville1 stop$156
Lexington
Lexington1 stop$186
Nashville
Nashville1 stop$156

Good to know

Low season

January

High season

November

Cheapest flight

$47
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago Midway Airport to Knoxville

FAQs - booking Kentucky flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kentucky from Chicago Midway Airport 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 Midway 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 to Kentucky with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway 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 to Kentucky from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Kentucky

  • Morning departure is around 11% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to Kentucky

 
Need help choosing which airline to fly with from Midway 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
DeltaOverall score based on 10673 reviews
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
8.6Crew
Airline reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

6.0 GoodGary, May 2024MSP - TPA
Read more about Delta reviews

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

My experience with Spirit was perfect. Did not expect it to be this good

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

The boarding gate was moved so many times that I missed my flight. No attendants would help me. The wrong gate was even on my boarding pass. I had to repurchase everything. I’ll never fly again. Really a terrible day as I had planned to see a former student who is dying in Louisville Never ever will I forget that day. Your airline is totally uncaring.

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

Hated it I would not use Kayak or Spirit ever again.

They stuck us with multiple extra fees. I will never fly spirit again

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Book cheap flights from Chicago to Kentucky

Recent round-trip flight deals

6/7sex
nonstopAllegiant Air
1h 25mMDW-TYS
6/10seg
nonstopAllegiant Air
1h 34mTYS-MDW
$75
6/14sex
nonstopAllegiant Air
1h 25mMDW-TYS
6/17seg
nonstopAllegiant Air
1h 34mTYS-MDW
$76
6/7sex
nonstop
1h 25mMDW-TYS
6/10seg
1 stop
15h 28mTYS-MDW
$134
9/11qua
1 stopFrontier
10h 17mMDW-TYS
9/18qua
1 stopFrontier
18h 35mTYS-MDW
$135
6/4ter
1 stopFrontier
9h 54mMDW-TYS
6/9dom
1 stopFrontier
10h 09mTYS-MDW
$138
6/17seg
1 stop
14h 44mMDW-TYS
6/21sex
nonstop
1h 34mTYS-MDW
$139
6/18ter
1 stopDelta
7h 12mMDW-CVG
6/25ter
1 stopDelta
4h 04mCVG-MDW
$156
7/30ter
1 stopDelta
3h 48mMDW-BNA
8/6ter
1 stopDelta
5h 51mBNA-MDW
$156
6/3seg
1 stopSouthwest
3h 10mMDW-BNA
6/5qua
nonstopSouthwest
1h 35mBNA-MDW
$206
5/28ter
nonstopSouthwest
1h 25mMDW-BNA
5/30qui
nonstopSouthwest
1h 30mBNA-MDW
$225

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Recent one-way flight deals

6/3seg
nonstopAllegiant Air
1h 28mMDW-TYS
$47
6/3seg
nonstopAllegiant Air
1h 28mMDW-TYS
$49
6/4ter
1 stopFrontier
9h 54mMDW-TYS
$61
6/19qua
1 stopDelta
5h 35mMDW-CVG
$78
6/14sex
1 stopDelta
3h 52mMDW-BNA
$78
5/30qui
1 stopFrontier
5h 37mMDW-TYS
$80
5/29qua
nonstopSouthwest
1h 25mMDW-BNA
$89
5/21ter
nonstopSouthwest
1h 25mMDW-BNA
$109
5/31sex
3 stops
21h 21mMDW-BNA
$171
7/22seg
2 stops
22h 35mMDW-BNA
$177

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Last minute flights from Midway to Kentucky

Last minute flight, train and bus deals

5/21ter
nonstopSouthwest
1h 25mMDW-BNA
5/23qui
nonstopSouthwest
1h 30mBNA-MDW
$234
5/21ter
nonstopSouthwest
1h 25mMDW-BNA
5/23qui
multi-stopSouthwest
5h 10mBNA-MDW
$243
5/21ter
multi-stopDelta
3h 42mMDW-BNA
5/22qua
multi-stopDelta
6h 35mBNA-MDW
$256
5/20seg
multi-stop
11h 27mMDW-TYS
5/27seg
nonstop
1h 32mTYS-MDW
$276
5/19dom
multi-stopDelta
6h 33mMDW-TYS
5/27seg
multi-stopDelta
3h 25mTYS-MDW
$283
5/17sex
multi-stopFrontier
14h 01mMDW-TYS
5/24sex
multi-stopFrontier
25h 23mTYS-MDW
$288
5/18sáb
multi-stopFrontier
10h 32mMDW-TYS
5/20seg
multi-stopFrontier
23h 34mTYS-MDW
$291
5/17sex
multi-stopAllegiant Air
15h 39mMDW-CVG
5/20seg
multi-stopAllegiant Air
13h 42mCVG-MDW
$545
5/17sex
multi-stopAllegiant Air
15h 39mMDW-CVG
5/20seg
multi-stopAllegiant Air
13h 42mCVG-MDW
$550
5/19dom
multi-stop
28h 50mMDW-BNA
5/23qui
multi-stop
20h 09mBNA-MDW
$716

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Chicago Midway Airport - Kentucky Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Kentucky - Chicago Midway Airport

Cabin classes: