$49 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 10/14. 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

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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Flight Deals

Cheap Flights from Midway to Kentucky

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisvillenonstop$97
Lexington
Lexington1 stop$271
Nashville
Nashvillenonstop$97
Louisville
Louisvillenonstop$97
Lexington
Lexington1 stop$271
Nashville
Nashvillenonstop$97

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

Mon, Oct 13 - Mon, Oct 20
Southwest Logo
9:30 pm - 10:55 pmMDW-BNA
1h 25mnonstop
Southwest Logo
9:45 pm - 11:15 pmBNA-MDW
1h 30mnonstop
$97Southwest
Find Deal
Mon, Nov 17 - Tue, Nov 18
Southwest Logo
10:00 am - 12:25 pmMDW-SDF
1h 25mnonstop
Southwest Logo
6:45 am - 7:00 amSDF-MDW
1h 15mnonstop
$97Southwest
Find Deal
Fri, Oct 24 - Mon, Oct 27
Allegiant Air Logo
2:45 pm - 5:09 pmMDW-TYS
1h 24mnonstop
Allegiant Air Logo
7:02 pm - 7:34 pmTYS-MDW
1h 32mnonstop
$125Allegiant Air
Find Deal
Fri, Oct 24 - Mon, Oct 27
Allegiant Air Logo
2:45 pm - 5:09 pmMDW-TYS
1h 24mnonstop
Allegiant Air Logo
7:02 pm - 7:34 pmTYS-MDW
1h 32mnonstop
$127Allegiant Air
Find Deal
Mon, Sep 29 - Thu, Oct 2
Frontier Logo
8:15 am - 7:27 pmMDW-BNA
11h 12m1 stop
Frontier Logo
8:14 pm - 7:11 amBNA-MDW
10h 57m1 stop
$145Frontier
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Thu, Oct 23 - Fri, Oct 24
Frontier Logo
6:24 pm - 10:40 amMDW-BNA
16h 16m1 stop
Frontier Logo
1:53 pm - 11:03 pmBNA-MDW
9h 10m1 stop
$146Frontier
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Mon, Oct 20 - Fri, Oct 24
Delta Logo
9:35 am - 12:58 pmMDW-BNA
3h 23m1 stop
Delta Logo
6:00 am - 12:28 pmBNA-MDW
6h 28m1 stop
$177Delta
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Fri, Nov 7 - Mon, Nov 17
Multiple Airlines Logo
2:57 pm - 5:22 pmMDW-TYS
1h 25mnonstop
Multiple Airlines Logo
2:22 pm - 8:31 pmTYS-MDW
7h 09m1 stop
$181Multiple Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
Delta Logo
5:04 pm - 12:01 amMDW-SDF
5h 57m1 stop
Delta Logo
2:33 pm - 6:25 pmSDF-MDW
4h 52m1 stop
$184Delta
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Fri, Nov 7 - Thu, Nov 13
Multiple Airlines Logo
2:57 pm - 5:22 pmMDW-TYS
1h 25mnonstop
Multiple Airlines Logo
7:17 pm - 11:30 amTYS-MDW
17h 13m1 stop
$184Multiple Airlines
Find Deal
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 $97 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 $97.

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 August, when tickets cost $213 (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 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 Tuesdays and the most expensive ones on Mondays.

Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly with an average 12% increase in price.
Flight from Chicago Midway Airport to Nashville

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 $275 on average. Morning departures are around 35% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the morning, which is peak travel time and where the average cost of a ticket is $372.

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 $98 one-way - $197 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 4242 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

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

Information on your arrival and departure airports

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