$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 2/14. 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, 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$196
Lexington
Lexington1 stop$209
Nashville
Nashvillenonstop$194
Louisville
Louisvillenonstop$196
Lexington
Lexington1 stop$209
Nashville
Nashvillenonstop$194

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

Sat, Feb 28 - Sat, Mar 7
Southwest Logo
8:35 pm - 10:45 pm
MDW
-
CVG
1h 10mnonstop
Southwest Logo
8:25 pm - 8:35 pm
CVG
-
MDW
1h 10mnonstop
$143Southwest
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
3:00 pm - 12:59 am
MDW
-
CVG
8h 59m
1 stop
Frontier Logo
1:07 pm - 10:29 pm
CVG
-
MDW
10h 22m
1 stop
$148Frontier
Thu, Feb 19 - Mon, Feb 23
Frontier Logo
9:05 am - 5:32 pm
MDW
-
CVG
7h 27m
1 stop
Frontier Logo
1:07 pm - 7:47 pm
CVG
-
MDW
7h 40m
1 stop
$149Frontier
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
7:45 am - 2:00 pm
MDW
-
CVG
5h 15m
1 stop
Southwest Logo
8:25 pm - 8:35 pm
CVG
-
MDW
1h 10mnonstop
$153Southwest
Thu, Feb 5 - Sun, Feb 8
Frontier Logo
6:20 am - 11:55 am
MDW
-
CVG
28h 35m
1 stop
Frontier Logo
12:00 pm - 11:45 am
CVG
-
MDW
24h 45m
1 stop
$154Frontier
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
7:45 am - 2:00 pm
MDW
-
CVG
5h 15m
1 stop
Southwest Logo
5:45 pm - 11:00 pm
CVG
-
MDW
6h 15m
1 stop
$163Southwest
Thu, Mar 5 - Tue, Mar 10
Southwest Logo
7:15 pm - 9:30 pm
MDW
-
CVG
1h 15mnonstop
Southwest Logo
7:35 pm - 7:45 pm
CVG
-
MDW
1h 10mnonstop
$164Southwest
Fri, Feb 13 - Mon, Feb 16
Frontier Logo
6:00 am - 5:32 pm
MDW
-
CVG
10h 32m
1 stop
Frontier Logo
1:07 pm - 7:47 pm
CVG
-
MDW
7h 40m
1 stop
$166Frontier
Thu, Feb 19 - Sun, Mar 1
Delta Logo
12:45 pm - 8:42 pm
MDW
-
LEX
6h 57m
1 stop
Delta Logo
6:00 am - 9:54 am
LEX
-
MDW
4h 54m
1 stop
$209Delta
Wed, Mar 4 - Mon, Mar 9
Delta Logo
6:00 am - 12:17 pm
MDW
-
TRI
5h 17m
1 stop
Delta Logo
7:17 pm - 10:31 pm
TRI
-
MDW
4h 14m
1 stop
$209Delta
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 $152 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 $152.

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 $208 on average.

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 seasonDecember
Cheapest flight$67
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 79% 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.

  • 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 $270 on average. Morning departures are around 2% 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 $329.

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 $158 one-way - $304 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 4267 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

10.0 ExcellentJoseph, Jan 2026
BWI - RIC
Read more Southwest reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)