$39 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 8/4. 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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Flights Deals

Best Kentucky Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Louisville
Louisvillenonstop$77
Lexington
Lexington1 stop$209
Nashville
Nashvillenonstop$77
Louisville
Louisvillenonstop$77
Lexington
Lexington1 stop$209
Nashville
Nashvillenonstop$77

Cheap Flights from Midway to Kentucky

 
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, Aug 7 - Mon, Aug 11
Southwest Logo
5:40 am - 7:05 amMDW-BNA
1h 25mnonstop
Southwest Logo
1:10 pm - 2:45 pmBNA-MDW
1h 35mnonstop
$77Southwest
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Thu, Aug 7 - Mon, Aug 11
Southwest Logo
8:35 pm - 10:50 pmMDW-SDF
1h 15mnonstop
Southwest Logo
1:15 pm - 1:30 pmSDF-MDW
1h 15mnonstop
$77Southwest
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Fri, Jul 25 - Mon, Jul 28
Allegiant Air Logo
2:54 pm - 5:20 pmMDW-TYS
1h 26mnonstop
Allegiant Air Logo
1:31 pm - 2:04 pmTYS-MDW
1h 33mnonstop
$77Allegiant Air
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Fri, Jul 25 - Mon, Jul 28
Allegiant Air Logo
2:54 pm - 5:20 pmMDW-TYS
1h 26mnonstop
Allegiant Air Logo
1:31 pm - 2:04 pmTYS-MDW
1h 33mnonstop
$78Allegiant Air
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Fri, Jun 27 - Mon, Jun 30
Frontier Logo
6:20 am - 2:20 pmMDW-CVG
7h 00m1 stop
Frontier Logo
6:05 am - 11:40 amCVG-MDW
6h 35m1 stop
$175Frontier
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Wed, Jul 30 - Wed, Aug 6
Delta Logo
6:00 am - 9:52 amMDW-BNA
3h 52m1 stop
Delta Logo
5:15 am - 9:45 amBNA-MDW
4h 30m1 stop
$177Delta
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Tue, Aug 5 - Sat, Aug 9
Delta Logo
1:46 pm - 7:01 pmMDW-SDF
4h 15m1 stop
Delta Logo
6:00 am - 9:45 amSDF-MDW
4h 45m1 stop
$177Delta
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Thu, Jun 26 - Sat, Jun 28
Frontier Logo
2:44 pm - 11:59 pmMDW-BNA
9h 15m1 stop
Frontier Logo
7:00 am - 8:53 pmBNA-MDW
13h 53m1 stop
$191Frontier
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Wed, Jul 2 - Sun, Jul 13
Logo
9:13 pm - 10:44 amMDW-SDF
12h 31m1 stop
Logo
6:53 pm - 2:04 pmSDF-MDW
20h 11m2 stops
$361
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Sat, Jul 26 - Mon, Jul 28
Logo
2:44 pm - 4:29 pmMDW-TYS
24h 45m1 stop
Logo
1:31 pm - 2:04 pmTYS-MDW
1h 33mnonstop
$385
Find Deal
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Kentucky.

The cheapest ticket to Kentucky from Chicago Midway Airport found in the last 72 hours was to Louisville, at $114 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 $114.

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 $222 (return) on average. On the other hand, the most expensive months are January and November, when the average cost of round-trip tickets is $633 and $602 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 Saturday 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 Wednesdays and the most expensive ones on Saturdays.

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Good to know

Low seasonJanuary
High seasonOctober
Cheapest flight$39
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 15% 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 at night, when round-trip flights cost $284 on average. Morning departures are around 3% cheaper than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the evening, which is peak travel time and where the average cost of a ticket is $384.

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 $118 one-way - $220 round-trip

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 4285 reviews
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
8.2Boarding
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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