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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 7/1. 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 7/10
Wed 7/17

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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$219
Lexington
Lexington1 stop$348
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% more expensive 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 10295 reviews
7.9Comfort
7.4Food
8.2Boarding
8.6Crew
8.0Entertainment
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

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!

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

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

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

I appreciated the upgrade to free cary-on bag and seat selection at no charge

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.

Book cheap flights from Chicago to Kentucky

Recent round-trip flight deals

7/12Fri
nonstop
1h 26mMDW-TYS
7/15Mon
1 stop
23h 10mTYS-MDW
$140
6/21Fri
nonstop
1h 25mMDW-TYS
6/27Thu
1 stop
10h 09mTYS-MDW
$155
8/6Tue
1 stopDelta
3h 35mMDW-BNA
8/13Tue
1 stopDelta
6h 42mBNA-MDW
$156
8/1Thu
1 stopFrontier
10h 17mMDW-CVG
8/5Mon
1 stopFrontier
11h 57mCVG-MDW
$158
7/5Fri
nonstop
1h 26mMDW-TYS
7/12Fri
1 stop
24h 24mTYS-MDW
$159
6/21Fri
1 stopFrontier
7h 26mMDW-CVG
6/25Tue
1 stopFrontier
7h 10mCVG-MDW
$166
7/30Tue
1 stopDelta
3h 55mMDW-BNA
8/6Tue
1 stopDelta
6h 42mBNA-MDW
$176
6/28Fri
nonstopAllegiant Air
1h 25mMDW-TYS
6/30Sun
1 stopAllegiant Air
13h 30mTYS-MDW
$187
6/21Fri
nonstopAllegiant Air
1h 25mMDW-TYS
6/23Sun
1 stopAllegiant Air
13h 30mTYS-MDW
$215
7/30Tue
3 stopsWestJet
25h 16mMDW-BNA
8/6Tue
3 stopsWestJet
24h 43mBNA-MDW
$1,106

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Recent one-way flight deals

7/1Mon
nonstopAllegiant Air
1h 25mMDW-TYS
$47
6/24Mon
nonstopAllegiant Air
1h 25mMDW-TYS
$52
6/24Mon
1 stopFrontier
18h 56mMDW-TYS
$64
6/18Tue
1 stopFrontier
6h 59mMDW-CVG
$67
7/16Tue
1 stopDelta
3h 42mMDW-CVG
$78
7/9Tue
1 stopDelta
3h 50mMDW-BNA
$78
7/1Mon
2 stops
24h 43mMDW-BNA
$139
7/22Mon
2 stops
8h 04mMDW-SDF
$158
7/23Tue
3 stopsWestJet
34h 36mMDW-TYS
$472
7/10Wed
3 stopsWestJet
27h 20mMDW-CVG
$487

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Last minute flights from Midway to Kentucky

Last minute flight, train and bus deals

6/10Mon
nonstopAllegiant Air
1h 25mMDW-TYS
6/24Mon
nonstopAllegiant Air
1h 34mTYS-MDW
$118
6/14Fri
multi-stop
14h 35mMDW-TYS
6/17Mon
nonstop
1h 34mTYS-MDW
$183
6/13Thu
multi-stopFrontier
6h 16mMDW-CVG
6/15Sat
multi-stopFrontier
14h 42mCVG-MDW
$206
6/13Thu
multi-stopFrontier
9h 47mMDW-CVG
6/16Sun
multi-stopFrontier
6h 52mCVG-MDW
$207
6/14Fri
multi-stopFrontier
12h 19mMDW-CVG
6/15Sat
multi-stopFrontier
14h 42mCVG-MDW
$223
6/14Fri
multi-stopFrontier
14h 35mMDW-TYS
6/17Mon
multi-stopFrontier
19h 29mTYS-MDW
$240
6/15Sat
multi-stopDelta
3h 49mMDW-BNA
6/16Sun
multi-stopDelta
4h 26mBNA-MDW
$386
6/12Wed
multi-stopDelta
4h 44mMDW-BNA
6/19Wed
multi-stopDelta
6h 43mBNA-MDW
$417
6/14Fri
multi-stopWestJet
30h 36mMDW-BNA
6/16Sun
multi-stopWestJet
19h 49mBNA-MDW
$1,786
6/13Thu
multi-stopWestJet
21h 45mMDW-BNA
6/16Sun
multi-stopWestJet
19h 49mBNA-MDW
$1,859

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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: