$65 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 5/13. 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$241
Lexington
Lexington1 stop$299
Nashville
Nashville2 stops$222
Louisville
Louisvillenonstop$241
Lexington
Lexington1 stop$299
Nashville
Nashville2 stops$222

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, Apr 2 - Mon, Apr 6
Southwest Logo
7:15 pm - 9:30 pm
MDW
-
CVG
1h 15mnonstop
Southwest Logo
8:15 pm - 8:30 pm
CVG
-
MDW
1h 15mnonstop
$211Southwest
Mon, Apr 27 - Mon, May 4
Frontier Logo
6:00 am - 6:36 pm
MDW
-
CVG
11h 36m
1 stop
Frontier Logo
9:29 pm - 11:12 am
CVG
-
MDW
14h 43m
2 stops
$212Frontier
Tue, Mar 31 - Thu, Apr 2
Southwest Logo
3:35 pm - 9:35 pm
MDW
-
CVG
5h 00m
1 stop
Southwest Logo
8:15 pm - 8:30 pm
CVG
-
MDW
1h 15mnonstop
$214Southwest
Wed, Jun 10 - Sat, Jun 13
Southwest Logo
6:15 pm - 8:25 pm
MDW
-
CVG
1h 10mnonstop
Southwest Logo
7:10 pm - 7:20 pm
CVG
-
MDW
1h 10mnonstop
$215Southwest
Thu, Apr 30 - Tue, May 5
Frontier Logo
6:00 am - 6:05 pm
MDW
-
CVG
11h 05m
1 stop
Frontier Logo
12:12 pm - 10:02 pm
CVG
-
MDW
10h 50m
1 stop
$221Frontier
Tue, Apr 7 - Wed, Apr 8
Southwest Logo
4:50 pm - 9:15 pm
MDW
-
CVG
3h 25m
1 stop
Southwest Logo
7:05 am - 2:55 pm
CVG
-
MDW
8h 50m
2 stops
$222Southwest
Sun, May 17 - Thu, May 21
Allegiant Air Logo
9:16 am - 7:55 pm
MDW
-
TYS
9h 39m
1 stop
Allegiant Air Logo
1:22 pm - 1:57 pm
TYS
-
MDW
1h 35mnonstop
$232Allegiant Air
Fri, May 22 - Sun, May 24
Allegiant Air Logo
9:30 pm - 10:18 pm
MDW
-
TYS
23h 48m
1 stop
Allegiant Air Logo
1:22 pm - 1:57 pm
TYS
-
MDW
1h 35mnonstop
$236Allegiant Air
Sat, Apr 4 - Fri, Apr 17
Delta Logo
6:00 am - 1:00 pm
MDW
-
TRI
6h 00m
1 stop
Delta Logo
7:19 pm - 10:28 pm
TRI
-
MDW
4h 09m
1 stop
$267Delta
Wed, Apr 8 - Wed, Apr 22
Delta Logo
10:45 am - 6:27 pm
MDW
-
TRI
6h 42m
1 stop
Delta Logo
7:19 pm - 10:28 pm
TRI
-
MDW
4h 09m
1 stop
$287Delta
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 $233 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 $233.

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 $255 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 at night, which is peak travel time and where the average cost of a ticket is $340.

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’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.

Find deals

Good to know

Low seasonDecember
Cheapest flight$65
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 50% increase in price.
Flight from Chicago Midway Airport to Cincinnati

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 $140 one-way - $288 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 4318 reviews
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)