$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 1/12. 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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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$209
Nashville
Nashvillenonstop$97
Louisville
Louisvillenonstop$97
Lexington
Lexington1 stop$209
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

Thu, Dec 4 - Mon, Dec 8
Southwest Logo
8:30 pm - 10:00 pmMDW-BNA
1h 30mnonstop
Southwest Logo
7:40 am - 9:25 amBNA-MDW
1h 45mnonstop
$97Southwest
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Thu, Dec 4 - Mon, Dec 8
Southwest Logo
8:50 pm - 11:05 pmMDW-SDF
1h 15mnonstop
Southwest Logo
1:50 pm - 2:05 pmSDF-MDW
1h 15mnonstop
$97Southwest
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Thu, Nov 27 - Thu, Dec 4
Multiple Airlines Logo
5:30 am - 7:57 pmMDW-BNA
14h 27m1 stop
Multiple Airlines Logo
2:00 pm - 9:58 pmBNA-MDW
7h 58m1 stop
$137Multiple Airlines
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Sun, Nov 9 - Thu, Nov 20
Frontier Logo
9:08 am - 5:54 pmMDW-BNA
8h 46m1 stop
Frontier Logo
10:20 am - 7:31 pmBNA-MDW
9h 11m1 stop
$143Frontier
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Mon, Nov 10 - Fri, Nov 14
Multiple Airlines Logo
8:00 am - 11:14 pmMDW-TYS
14h 14m1 stop
Multiple Airlines Logo
2:02 pm - 2:37 pmTYS-MDW
1h 35mnonstop
$148Multiple Airlines
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Thu, Dec 4 - Mon, Dec 8
Delta Logo
9:34 am - 6:52 pmMDW-SDF
8h 18m2 stops
Delta Logo
7:50 am - 6:18 pmSDF-MDW
11h 28m2 stops
$167Delta
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Fri, Nov 21 - Wed, Nov 26
Allegiant Air Logo
2:11 pm - 4:36 pmMDW-TYS
1h 25mnonstop
Allegiant Air Logo
6:18 pm - 6:54 pmTYS-MDW
1h 36mnonstop
$167Allegiant Air
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Thu, Nov 13 - Sun, Nov 16
Frontier Logo
10:12 am - 12:19 pmMDW-BNA
26h 07m1 stop
Frontier Logo
11:10 am - 8:32 amBNA-MDW
21h 22m1 stop
$169Frontier
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Mon, Nov 24 - Wed, Dec 3
Delta Logo
1:15 pm - 4:49 pmMDW-BNA
3h 34m1 stop
Delta Logo
12:48 pm - 4:34 pmBNA-MDW
3h 46m1 stop
$173Delta
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Mon, Nov 24 - Wed, Nov 26
Allegiant Air Logo
2:11 pm - 4:36 pmMDW-TYS
1h 25mnonstop
Allegiant Air Logo
6:18 pm - 6:54 pmTYS-MDW
1h 36mnonstop
$174Allegiant Air
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 $201 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 $201.

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 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 32% increase in price.
Most popular time to fly with an average 17% 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 $276 on average. Morning departures are around 32% 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 $365.

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 $133 one-way - $227 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 4243 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

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

Information on your arrival and departure airports

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