Find flights
Deals
When to book
FAQs & Tips
Airlines

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 8/23. 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
Wed 6/12
Wed 6/19

Search hundreds of travel sites at once for deals on flights to Kentucky

In the last 7 days travelers have searched 41,771,603 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

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

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

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$156
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 6% 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 10736 reviews
7.4Food
8.6Crew
8.0Entertainment
7.9Comfort
8.2Boarding
Airline reviews

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

2.0 MediocreDevan, May 2024AUS - BOS
Read more about Delta reviews

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.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

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

Arrived 3 hours early and never made it past baggage drop

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

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 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Book cheap flights from Chicago to Kentucky

Recent round-trip flight deals

6/7Fri
nonstopAllegiant Air
1h 25mMDW-TYS
6/10Mon
nonstopAllegiant Air
1h 34mTYS-MDW
$75
6/10Mon
nonstopAllegiant Air
1h 25mMDW-TYS
6/14Fri
nonstopAllegiant Air
1h 34mTYS-MDW
$77
6/7Fri
nonstop
1h 25mMDW-TYS
6/10Mon
1 stop
15h 28mTYS-MDW
$134
6/10Mon
nonstop
1h 25mMDW-TYS
6/14Fri
1 stop
14h 15mTYS-MDW
$140
5/30Thu
1 stopFrontier
5h 37mMDW-TYS
6/2Sun
1 stopFrontier
22h 54mTYS-MDW
$155
9/3Tue
1 stopDelta
2h 52mMDW-CVG
9/17Tue
1 stopDelta
7h 14mCVG-MDW
$156
7/30Tue
1 stopDelta
3h 48mMDW-BNA
8/6Tue
1 stopDelta
5h 51mBNA-MDW
$156
6/1Sat
1 stopFrontier
21h 24mMDW-TYS
6/2Sun
1 stopFrontier
22h 54mTYS-MDW
$164
6/18Tue
3 stopsWestJet
25h 41mMDW-BNA
6/23Sun
2 stopsWestJet
24h 41mBNA-MDW
$1,236
5/22Wed
3 stopsWestJet
23h 05mMDW-SDF
5/25Sat
3 stopsWestJet
23h 40mSDF-MDW
$1,236

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/23Fri
nonstopAllegiant Air
1h 29mMDW-TYS
$47
9/23Mon
nonstopAllegiant Air
1h 30mMDW-TYS
$50
9/27Fri
nonstopAllegiant Air
1h 30mMDW-TYS
$60
5/29Wed
1 stopFrontier
23h 28mMDW-TYS
$68
5/30Thu
1 stopFrontier
5h 37mMDW-TYS
$75
6/11Tue
1 stopDelta
4h 10mMDW-BNA
$78
6/11Tue
1 stopDelta
3h 06mMDW-SDF
$78
6/10Mon
2 stops
19h 49mMDW-SDF
$155
6/24Mon
2 stops
15h 51mMDW-BNA
$161
6/1Sat
3 stopsWestJet
24h 04mMDW-BNA
$298

Search by stops

Search by airline

Search by price

Last minute flights from Midway to Kentucky

Last minute flight, train and bus deals

5/17Fri
multi-stopFrontier
14h 01mMDW-TYS
5/19Sun
multi-stopFrontier
20h 28mTYS-MDW
$223
5/17Fri
multi-stopFrontier
14h 01mMDW-TYS
5/19Sun
multi-stopFrontier
20h 28mTYS-MDW
$225
5/18Sat
multi-stop
9h 49mMDW-TYS
5/27Mon
nonstop
1h 32mTYS-MDW
$266
5/18Sat
multi-stopFrontier
10h 32mMDW-TYS
5/27Mon
multi-stopFrontier
12h 15mTYS-MDW
$353
5/18Sat
multi-stopFrontier
10h 32mMDW-TYS
5/27Mon
multi-stopFrontier
20h 14mTYS-MDW
$355
5/18Sat
multi-stopDelta
5h 48mMDW-BNA
5/22Wed
multi-stopDelta
6h 35mBNA-MDW
$376
5/18Sat
multi-stopDelta
6h 04mMDW-TYS
5/27Mon
multi-stopDelta
3h 25mTYS-MDW
$388
5/16Thu
multi-stopAllegiant Air
24h 41mMDW-CVG
5/20Mon
multi-stopAllegiant Air
13h 42mCVG-MDW
$399
5/17Fri
multi-stopAllegiant Air
32h 10mMDW-CVG
5/20Mon
multi-stopAllegiant Air
13h 42mCVG-MDW
$442
5/18Sat
multi-stop
25h 09mMDW-TYS
5/27Mon
nonstop
1h 32mTYS-MDW
$675

Search by stops

Search by airline

Search by price

Chicago Midway Airport - Kentucky Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Kentucky - Chicago Midway Airport

Cabin classes: