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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 7/5. 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. 7/6
sáb. 7/13

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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$177
Lexington
Lexington1 stop$234
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 10368 reviews
7.9Comfort
8.6Crew
8.0Entertainment
7.4Food
8.2Boarding
Airline reviews

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

4.0 OkayDavwinder Singh, Jun 2024SEA - ATL
Read more about Delta reviews

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Book cheap flights from Chicago to Kentucky

Recent round-trip flight deals

7/5vie.
nonstopAllegiant Air
1h 26mMDW-TYS
7/8lun.
nonstopAllegiant Air
1h 32mTYS-MDW
$75
6/21vie.
nonstopAllegiant Air
1h 25mMDW-TYS
6/24lun.
nonstopAllegiant Air
1h 34mTYS-MDW
$77
6/21vie.
nonstop
1h 25mMDW-TYS
6/24lun.
1 stop
15h 28mTYS-MDW
$141
7/11jue.
1 stop
21h 41mMDW-TYS
7/15lun.
nonstop
1h 32mTYS-MDW
$154
7/30mar.
1 stopDelta
3h 55mMDW-BNA
8/6mar.
1 stopDelta
6h 42mBNA-MDW
$156
7/30mar.
1 stopFrontier
6h 15mMDW-BNA
8/6mar.
2 stopsFrontier
21h 00mBNA-MDW
$173
7/30mar.
1 stopDelta
3h 55mMDW-BNA
8/6mar.
1 stopDelta
6h 42mBNA-MDW
$176
7/11jue.
1 stopFrontier
21h 41mMDW-TYS
7/15lun.
1 stopFrontier
23h 10mTYS-MDW
$198
8/8jue.
nonstopSouthwest
1h 25mMDW-BNA
8/11dom.
nonstopSouthwest
1h 30mBNA-MDW
$224
7/15lun.
nonstopSouthwest
1h 10mMDW-SDF
7/19vie.
nonstopSouthwest
1h 15mSDF-MDW
$225

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Recent one-way flight deals

7/5vie.
nonstopAllegiant Air
1h 26mMDW-TYS
$47
6/21vie.
nonstopAllegiant Air
1h 25mMDW-TYS
$49
7/1lun.
1 stopDelta
7h 11mMDW-CVG
$78
9/28sáb.
1 stopDelta
3h 32mMDW-BNA
$78
8/8jue.
1 stopFrontier
8h 02mMDW-BNA
$87
6/13jue.
1 stopFrontier
21h 49mMDW-TYS
$90
7/1lun.
2 stops
24h 43mMDW-BNA
$141
7/1lun.
3 stops
21h 10mMDW-BNA
$156
6/25mar.
3 stopsWestJet
18h 46mMDW-LEX
$395
7/4jue.
3 stopsWestJet
26h 07mMDW-TYS
$424

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Last minute flights from Midway to Kentucky

Last minute flight, train and bus deals

6/10lun.
multi-stop
18h 56mMDW-TYS
6/14vie.
nonstop
1h 34mTYS-MDW
$273
6/10lun.
multi-stopFrontier
18h 56mMDW-TYS
6/24lun.
multi-stopFrontier
19h 29mTYS-MDW
$299
6/7vie.
multi-stopFrontier
14h 35mMDW-TYS
6/9dom.
multi-stopFrontier
10h 09mTYS-MDW
$312
6/10lun.
nonstopSouthwest
1h 25mMDW-BNA
6/13jue.
nonstopSouthwest
1h 30mBNA-MDW
$405
6/11mar.
multi-stopDelta
3h 06mMDW-SDF
6/12mié.
multi-stopDelta
4h 51mSDF-MDW
$408
6/11mar.
multi-stopDelta
9h 49mMDW-SDF
6/12mié.
multi-stopDelta
3h 44mSDF-MDW
$413
6/10lun.
multi-stopSouthwest
9h 05mMDW-BNA
6/13jue.
nonstopSouthwest
1h 30mBNA-MDW
$415
6/10lun.
multi-stopSouthwest
10h 15mMDW-BNA
6/13jue.
nonstopSouthwest
1h 30mBNA-MDW
$420
6/10lun.
multi-stopFrontier
18h 56mMDW-TYS
6/14vie.
multi-stopFrontier
14h 15mTYS-MDW
$427
6/10lun.
multi-stopAllegiant Air
22h 57mMDW-LEX
6/12mié.
multi-stopAllegiant Air
16h 28mLEX-MDW
$433

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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: