$73 Find Cheap Flights from Chicago Midway Airport to Kentucky

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Kentucky departing on 6/2. 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.
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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$179
Lexington
Lexington1 stop$209
Nashville
Nashvillenonstop$145
Louisville
Louisvillenonstop$179
Lexington
Lexington1 stop$209
Nashville
Nashvillenonstop$145

Cheap Flight Deals from Midway to Kentucky (MDW-USKY)

 
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.

Recent round-trip flight deals from Midway to Kentucky

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Kentucky.
Discover the best prices for you by selecting your travel dates on KAYAK.
Allegiant Air Logo
2:53 pm - 5:18 pmMDW-TYS
1h 25mnonstop
Allegiant Air Logo
1:29 pm - 2:03 pmTYS-MDW
1h 34mnonstop
$80Allegiant Air
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Fri, Jun 20 - Mon, Jun 23
Allegiant Air Logo
7:00 pm - 9:28 pmMDW-TYS
1h 28mnonstop
Allegiant Air Logo
5:37 pm - 6:10 pmTYS-MDW
1h 33mnonstop
$83Allegiant Air
Find Deal
Fri, May 30 - Mon, Jun 2
Southwest Logo
8:30 pm - 10:00 pmMDW-BNA
1h 30mnonstop
Southwest Logo
6:55 pm - 8:30 pmBNA-MDW
1h 35mnonstop
$145Southwest
Find Deal
Fri, May 30 - Mon, Jun 2
Southwest Logo
9:35 pm - 11:05 pmMDW-BNA
1h 30mnonstop
Southwest Logo
5:25 am - 7:00 amBNA-MDW
1h 35mnonstop
$152Southwest
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Tue, Jul 15 - Fri, Jul 18
Delta Logo
10:25 am - 1:56 pmMDW-BNA
3h 31m1 stop
Delta Logo
9:26 am - 3:20 pmBNA-MDW
5h 54m1 stop
$177Delta
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Fri, May 30 - Mon, Jun 2
Delta Logo
10:25 am - 1:56 pmMDW-BNA
3h 31m1 stop
Delta Logo
10:15 am - 4:21 pmBNA-MDW
6h 06m1 stop
$179Delta
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Wed, Jun 4 - Sat, Jun 7
Frontier Logo
1:19 pm - 12:59 amMDW-CVG
10h 40m1 stop
Frontier Logo
5:45 am - 12:24 pmCVG-MDW
7h 39m1 stop
$180Frontier
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Thu, May 15 - Mon, May 19
Frontier Logo
6:20 am - 6:02 pmMDW-CVG
10h 42m1 stop
Frontier Logo
6:00 am - 10:41 pmCVG-MDW
17h 41m1 stop
$184Frontier
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Sat, May 24 - Sun, May 25
Logo
2:54 pm - 11:59 pmMDW-BNA
33h 05m3 stops
Logo
8:43 am - 9:41 amBNA-MDW
24h 58m2 stops
$352
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Fri, Jul 25 - Sun, Jul 27
Logo
2:53 pm - 9:39 pmMDW-BNA
30h 46m2 stops
Logo
8:20 am - 7:15 amBNA-MDW
22h 55m2 stops
$380
Find Deal
Mon, Jun 23 - Thu, Jun 26
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 $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’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 Tuesdays and the most expensive ones on Mondays.

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Good to know

Low seasonJuly
High seasonOctober
Cheapest flight$73
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 9% 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 $275 on average. Morning departures are around 10% 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 $428.

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 - $189 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 4294 reviews
8.2Boarding
7.1Food
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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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