HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kentucky

$67+ Cheap flights from Midway (MDW) to Kentucky

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Jan 28 — Feb 41
Wed 1/28
Wed 2/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Kentucky with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Midway to Kentucky

Cheapest flights from Midway to Kentucky
Explore the most affordable flight options available from Midway to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 29, 2025.

This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:08 pmMDW - LEX
1 stop3h 59mDelta
Sun 1/46:20 amLEX - MDW
1 stop3h 29mDelta
Deal found 12/27$331
This Southwest deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/289:30 amMDW - SDF
Nonstop1h 15mSouthwest
Thu 1/296:45 amSDF - MDW
Nonstop1h 25mSouthwest
Deal found 12/27$468
This Delta deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:08 pmMDW - SDF
1 stop3h 50mDelta
Thu 1/2910:41 amSDF - MDW
2 stops8h 55mDelta
Deal found 12/27$493
This Delta deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:50 amMDW - TYS
1 stop5h 24mDelta
Fri 1/26:00 amTYS - MDW
1 stop6h 58mDelta
Deal found 12/28$499
This Kiwi.com deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - CVG
1 stop18h 42mFrontier
Sun 1/42:50 pmCVG - MDW
1 stop23h 31mFrontier
Deal found 12/27$520
This Kiwi.com deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - CVG
1 stop18h 42mFrontier
Sat 1/31:53 pmCVG - MDW
1 stop9h 19mFrontier
Deal found 12/27$537
This Kiwi.com deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - BNA
1 stop19h 39mMultiple Airlines
Mon 1/58:37 pmBNA - MDW
1 stop15h 16mMultiple Airlines
Deal found 12/27$557
This Delta deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:08 pmMDW - CVG
1 stop3h 49mDelta
Mon 1/52:22 pmCVG - MDW
1 stop4h 12mDelta
Deal found 12/28$564
This Kiwi.com deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - CVG
1 stop8h 56mFrontier
Fri 1/26:49 pmCVG - MDW
1 stop19h 20mFrontier
Deal found 12/27$585
This Southwest deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:20 pmMDW - CVG
Nonstop1h 15mSouthwest
Thu 1/17:00 amCVG - MDW
Nonstop1h 15mSouthwest
Deal found 12/28$589
This Southwest deal was found by Cheapflights users on 12/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:20 pmMDW - CVG
Nonstop1h 15mSouthwest
Sun 1/46:40 amCVG - MDW
Nonstop1h 15mSouthwest
Deal found 12/27$602
This Southwest deal was found by Cheapflights users on 12/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:25 pmMDW - CVG
2 stops5h 55mSouthwest
Sat 1/31:00 pmCVG - MDW
Nonstop1h 05mSouthwest
Deal found 12/28$604

Find flight deals from Midway to Kentucky

Keep the following information in mind while searching for Midway to Kentucky flight deals. Data was last updated December 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$152
(Southwest)

One-way from

$67
(Kiwi.com)

Popular in

February

Cheapest in

August

Average price

$294
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
Search Deals
From Chicago Midway to Kentucky
Search Deals
One-way flight from Chicago Midway to Kentucky
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kentucky that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kentucky that are best for you.

Fly from

Midway

Fly to

Kentucky

Route

Depart

Return

Price

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Fri 2/6

1:00 pm-11:26 pm

1 stop9h 26m

Cincinnati Cinci./N. Kentucky

Sun 2/8

7:00 am-7:52 pm

1 stop13h 52m

$169

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 3/14

9:30 pm-11:00 pm

Nonstop1h 30m

Nashville Intl

Mon 3/16

5:10 am-6:45 am

Nonstop1h 35m

$175

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Fri 1/23

1:00 pm-11:26 pm

1 stop9h 26m

Cincinnati Cinci./N. Kentucky

Sun 1/25

5:39 pm-7:58 pm

1 stop27h 19m

$180

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Sat 1/17

5:00 pm-11:06 pm

1 stop5h 06m

Louisville Intl

Mon 1/19

6:23 am-1:09 pm

1 stop7h 46m

$191

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 1/24

8:40 am-10:20 am

Nonstop1h 40m

Nashville Intl

Sat 1/24

3:45 pm-5:20 pm

Nonstop1h 35m

$191

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Sat 1/17

6:40 am-12:35 pm

1 stop4h 55m

Louisville Intl

Mon 1/19

6:25 am-6:55 am

Nonstop1h 30m

$193

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Fri 2/20

6:00 am-5:32 pm

1 stop10h 32m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-7:47 pm

1 stop7h 40m

$200

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/19

6:15 am-4:37 pm

1 stop9h 22m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-7:47 pm

1 stop7h 40m

$200

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Sun 1/18

10:00 am-12:15 pm

Nonstop1h 15m

Louisville Intl

Mon 1/19

6:25 am-6:55 am

Nonstop1h 30m

$203

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Thu 1/22

10:48 am-3:49 pm

1 stop4h 01m

Lexington Blue Grass

Sun 1/25

6:40 pm-10:22 pm

1 stop4h 42m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Midway to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Kentucky

What is the cheapest month to book a flight from Chicago Midway Airport to Kentucky?

Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Kentucky (average of $124). Flying from Chicago Midway Airport to Kentucky in January is currently the most expensive (average of $633). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MDW to KY?

Find hourly flight availability from Midway to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 29, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 11% on flights from Chicago Midway Airport to Kentucky by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Chicago Midway Airport to Kentucky?

Use this chart to determine the cheapest time to fly round-trip from Midway to Kentucky. Price data was last updated on December 27, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Kentucky flight should consider departing on Monday evenings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated December 29, 2025.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Kentucky to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,252 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Kentucky?

    There are many flights that can get you from Chicago Midway Airport to Kentucky in 1h 30m. Fly via Frontier, Southwest, or Delta to get the fastest option. Chicago Midway Airport and Kentucky are separated by a distance of 395 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago Midway Airport to Kentucky?

    While some choose either Chicago Midway - Cincinnati Cinci./N. Kentucky or Chicago Midway - Knoxville McGhee Tyson, Chicago Midway - Nashville Intl is the most popular route from Chicago Midway Airport to Kentucky.

  • Can I find deals for flights from Midway to Kentucky that include hotel bookings?

    Yes. In addition to deals on Midway to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Kentucky.

  • Can I find deals for business class flights from Midway to Kentucky?

    Yes. Cheapflights offers flight deals from Midway to Kentucky by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Kentucky?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Kentucky (average of $124). Flying from Chicago Midway Airport to Kentucky in January is currently the most expensive (average of $633). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Midway to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Orlando flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Tampa flights
O'Hare Intl to Newark flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Denver flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Seattle flights
O'Hare Intl to San Diego flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Santa Ana flights
Midway to Orlando flights
Midway to Las Vegas flights
O'Hare Intl to New Orleans flights
Midway to Miami flights
Midway to Los Angeles flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Lauderdale flights
O'Hare Intl to Sarasota flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Austin flights
Midway to John F Kennedy Intl flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Key West flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Ontario flights
O'Hare Intl to Love Field flights
O'Hare Intl to Reagan-National flights
Midway to Tampa flights
O'Hare Intl to Baltimore flights
Midway to LaGuardia flights
Midway to Atlanta flights
O'Hare Intl to Nashville flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Kahului flights
O'Hare Intl to Charleston flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Reno flights
O'Hare Intl to Boston flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Tucson flights

Top airline flying from Midway to Kentucky

Discover the top airline that operate flights from Midway to Kentucky. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$124Average$404FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.