$51 Find Cheap Flights from Chicago Midway Airport to Kentucky

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 7/16. 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
1 adult, Economy, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kentucky, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Kentucky, as well as popular online travel agencies
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Cheap Flights from Midway to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisvillenonstop$256
Lexington
Lexington1 stop$269
Nashville
Nashvillenonstop$237
Louisville
Louisvillenonstop$256
Lexington
Lexington1 stop$269
Nashville
Nashvillenonstop$237

Book Cheap Midway to Kentucky Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Kentucky that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Kentucky

Thu, Jul 2 - Sun, Jul 5
Allegiant Air Logo
2:48 pm - 5:18 pm
MDW
-
TYS
1h 30mnonstop
Allegiant Air Logo
1:22 pm - 1:58 pm
TYS
-
MDW
1h 36mnonstop
$135Allegiant Air
Thu, Jun 25 - Sun, Jun 28
Allegiant Air Logo
2:46 pm - 5:14 pm
MDW
-
TYS
1h 28mnonstop
Allegiant Air Logo
1:22 pm - 1:56 pm
TYS
-
MDW
1h 34mnonstop
$139Allegiant Air
Sat, May 16 - Mon, May 18
Southwest Logo
7:40 am - 9:45 am
MDW
-
CVG
1h 05mnonstop
Southwest Logo
8:20 pm - 8:30 pm
CVG
-
MDW
1h 10mnonstop
$191Southwest
Wed, May 20 - Mon, May 25
Delta Logo
9:22 am - 3:14 pm
MDW
-
CVG
4h 52m
1 stop
Delta Logo
5:48 am - 11:56 am
CVG
-
MDW
7h 08m
1 stop
$194Delta
Wed, May 20 - Mon, May 25
Delta Logo
9:22 am - 6:57 pm
MDW
-
CVG
8h 35m
2 stops
Delta Logo
5:48 am - 11:56 am
CVG
-
MDW
7h 08m
1 stop
$199Delta
Sat, May 16 - Mon, May 18
Southwest Logo
7:45 am - 2:00 pm
MDW
-
CVG
5h 15m
1 stop
Southwest Logo
8:20 pm - 8:30 pm
CVG
-
MDW
1h 10mnonstop
$201Southwest
Mon, May 18 - Tue, May 26
Frontier Logo
6:00 am - 11:41 am
MDW
-
CVG
4h 41m
1 stop
Frontier Logo
12:12 pm - 10:02 pm
CVG
-
MDW
10h 50m
1 stop
$206Frontier
Wed, May 27 - Wed, Jun 3
Frontier Logo
12:04 pm - 11:38 pm
MDW
-
CVG
10h 34m
2 stops
Frontier Logo
12:46 pm - 10:02 pm
CVG
-
MDW
10h 16m
1 stop
$213Frontier
Thu, May 14 - Mon, May 18
Multiple Airlines Logo
9:16 am - 8:42 am
MDW
-
LEX
22h 26m
1 stop
Multiple Airlines Logo
9:45 pm - 10:02 pm
LEX
-
MDW
25h 17m
2 stops
$304Multiple Airlines
Sat, May 23 - Sat, May 30
Multiple Airlines Logo
11:59 am - 8:47 am
MDW
-
LEX
19h 48m
2 stops
Multiple Airlines Logo
11:48 am - 8:24 am
LEX
-
MDW
21h 36m
1 stop
$338Multiple Airlines
Booking Insights

KAYAK's insights & trends for Midway to Kentucky flights

Get data-powered insights and trends into flights from Midway 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 Midway Airport to Kentucky?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Kentucky departing in May.

What is the cheapest Chicago Midway Airport to Kentucky flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Kentucky from Chicago Midway Airport found in the last 72 hours was to Louisville, at $292 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Louisville (SDF), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $292.

What is the cheapest time of day to fly to Kentucky?

The average price for all round-trip flights from Chicago Midway Airport to Kentucky depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Kentucky is generally in the evening, when round-trip flights cost $249 on average. Morning departures are around 19% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally at night, which is peak travel time and where the average cost of a ticket is $351.

Can I save money by flying with a layover from Chicago Midway Airport to Kentucky?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

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 $252 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Kentucky, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to Kentucky is January, when tickets cost $0 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $582 and $263 respectively.

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

The average price of all round-trip flights from Chicago Midway Airport to Kentucky clicked on KAYAK for each day over the last 12 months.

When flying from Chicago Midway Airport to Kentucky, you should consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to Chicago Midway Airport, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

Good to know

Low seasonDecember
Cheapest flight$57
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 44% 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 from Chicago Midway Airport 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 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 from Chicago Midway Airport 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 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 from Chicago Midway Airport to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Kentucky

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Nashville $168 one-way - $336 round-trip

Reviews of the top airline flying from Midway to Kentucky

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Kentucky. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
SouthwestOverall score based on 4314 reviews
7.0Food
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Everything you need to know for your flight from Midway to Kentucky

Information on your arrival and departure airports