$67 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 1/6. 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$171
Lexington
Lexington1 stop$297
Nashville
Nashvillenonstop$152
Louisville
Louisvillenonstop$171
Lexington
Lexington1 stop$297
Nashville
Nashvillenonstop$152

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

Tue, Feb 17 - Sat, Feb 28
Southwest Logo
5:25 am - 7:00 am
MDW
-
BNA
1h 35mnonstop
Southwest Logo
5:45 pm - 7:25 pm
BNA
-
MDW
1h 40mnonstop
$152Southwest
Tue, Jan 13 - Tue, Jan 20
Delta Logo
1:28 pm - 5:04 pm
MDW
-
BNA
3h 36m1 stop
Delta Logo
6:30 am - 11:59 am
BNA
-
MDW
5h 29m1 stop
$157Delta
Wed, Jan 7 - Thu, Jan 8
Southwest Logo
10:05 am - 3:55 pm
MDW
-
BNA
5h 50m1 stop
Southwest Logo
7:25 am - 9:10 am
BNA
-
MDW
1h 45mnonstop
$162Southwest
Sat, Jan 10 - Wed, Jan 14
Southwest Logo
8:40 am - 10:20 am
MDW
-
BNA
1h 40mnonstop
Southwest Logo
7:35 am - 1:55 pm
BNA
-
MDW
6h 20m2 stops
$167Southwest
Wed, Jan 7 - Wed, Jan 7
Southwest Logo
6:00 am - 7:35 am
MDW
-
BNA
1h 35mnonstop
Southwest Logo
11:45 am - 1:20 pm
BNA
-
MDW
1h 35mnonstop
$171Southwest
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
10:00 am - 12:15 pm
MDW
-
SDF
1h 15mnonstop
Southwest Logo
6:45 am - 7:10 am
SDF
-
MDW
1h 25mnonstop
$171Southwest
Tue, Jan 13 - Wed, Jan 14
Multiple Airlines Logo
11:39 am - 8:29 am
MDW
-
BNA
20h 50m2 stops
Multiple Airlines Logo
5:50 pm - 10:32 am
BNA
-
MDW
16h 42m1 stop
$176Multiple Airlines
Tue, Jan 13 - Tue, Jan 20
Frontier Logo
6:30 pm - 6:50 pm
MDW
-
CVG
23h 20m1 stop
Frontier Logo
4:23 pm - 12:05 pm
CVG
-
MDW
20h 42m2 stops
$178Frontier
Mon, Jan 19 - Wed, Jan 21
Frontier Logo
10:07 am - 12:55 am
MDW
-
CVG
13h 48m1 stop
Frontier Logo
4:23 pm - 11:45 am
CVG
-
MDW
20h 22m2 stops
$190Frontier
Sun, Jan 11 - Mon, Jan 12
Multiple Airlines Logo
4:21 pm - 10:10 am
MDW
-
TYS
16h 49m1 stop
Multiple Airlines Logo
12:55 pm - 11:09 pm
TYS
-
MDW
11h 14m1 stop
$203Multiple 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.

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 $159 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 $159.

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 September, when tickets cost $139 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $633 and $601 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 Tuesday 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.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$67
Best time to beat the crowds but there is an average 42% increase in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago Midway Airport to Louisville

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.

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

    The cheapest time of day to fly to Kentucky is generally in the evening, when round-trip flights cost $273 on average. Morning departures are around 8% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $305.

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.
7.9
SouthwestOverall score based on 4250 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)