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$39+ 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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Midway to Kentucky

Keep the following information in mind while searching for Midway to Kentucky flight deals. Data was last updated August 14, 2025.

Round-trip from

$77
(Southwest)

One-way from

$39
(Southwest)

Popular in

February

Cheapest in

August

Average price

$173

Good round-trip deal

$151 or less

Good one-way deal

$38 or less
From Chicago Midway to Kentucky
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One-way flight from Chicago Midway to Kentucky
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Highest demand for flights based on searches. 16% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago Midway to Kentucky.
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Price to beat on a one-way flight from Chicago Midway to Kentucky.
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Find 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 August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/12. 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 9/3010:05 amMDW - SDF
Nonstop1h 20mSouthwest
Sat 10/44:25 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 8/12$77
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 9/412:15 pmMDW - BNA
1 stop4h 40mSouthwest
Thu 9/49:15 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 8/12$87
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 9/412:00 pmMDW - BNA
Nonstop1h 25mSouthwest
Mon 9/812:00 pmBNA - MDW
2 stops6h 05mSouthwest
Deal found 8/12$92
This Southwest deal was found by Cheapflights users on 8/13. 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.
Sat 9/139:45 amMDW - BNA
1 stop4h 15mSouthwest
Sat 9/133:00 pmBNA - MDW
1 stop5h 45mSouthwest
Deal found 8/13$97
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 9/67:30 pmMDW - SDF
Nonstop1h 15mSouthwest
Sun 9/77:00 amSDF - MDW
Nonstop1h 15mSouthwest
Deal found 8/12$114
This Southwest deal was found by Cheapflights users on 8/14. 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.
Thu 10/29:30 pmMDW - BNA
Nonstop1h 25mSouthwest
Sun 10/510:40 pmBNA - MDW
Nonstop1h 30mSouthwest
Deal found 8/14$117
This Cheapflightsfares deal was found by Cheapflights users on 8/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:50 pmMDW - TYS
Nonstop1h 31mAllegiant Air
Mon 9/291:50 pmTYS - MDW
Nonstop1h 36mAllegiant Air
Deal found 8/14$119
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Fri 9/197:50 pmMDW - TYS
Nonstop1h 31mAllegiant Air
Fri 10/310:44 amTYS - MDW
Nonstop1h 32mAllegiant Air
Deal found 8/13$125
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/197:50 pmMDW - TYS
Nonstop1h 31mAllegiant Air
Mon 9/226:24 pmTYS - MDW
Nonstop1h 36mAllegiant Air
Deal found 8/12$128
This Southwest deal was found by Cheapflights users on 8/11. 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 8/278:20 pmMDW - BNA
Nonstop1h 30mSouthwest
Tue 9/28:50 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 8/11$129
This Southwest deal was found by Cheapflights users on 8/13. 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.
Fri 9/195:40 amMDW - BNA
Nonstop1h 25mSouthwest
Sat 9/2012:10 pmBNA - MDW
2 stops6h 50mSouthwest
Deal found 8/13$132
This Southwest deal was found by Cheapflights users on 8/13. 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 9/75:35 amMDW - SDF
1 stop5h 50mSouthwest
Tue 9/93:50 pmSDF - MDW
1 stop5h 35mSouthwest
Deal found 8/13$134

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 August 14, 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

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 9/30

10:05 am-12:25 pm

Nonstop1h 20m

Louisville Intl

Sat 10/4

4:25 pm-4:40 pm

Nonstop1h 15m

$77

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 9/20

10:05 am-2:50 pm

1 stop4h 45m

Nashville Intl

Tue 9/23

7:20 am-8:55 am

Nonstop1h 35m

$87

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 9/16

2:05 pm-3:30 pm

Nonstop1h 25m

Nashville Intl

Thu 9/18

11:30 am-4:35 pm

1 stop5h 05m

$87

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 9/11

5:40 am-7:05 am

Nonstop1h 25m

Nashville Intl

Tue 9/16

9:55 am-3:20 pm

1 stop5h 25m

$87

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 10/23

9:55 am-1:10 pm

1 stop3h 15m

Nashville Intl

Mon 10/27

5:30 am-7:05 am

Nonstop1h 35m

$87

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 9/27

1:05 pm-6:15 pm

1 stop5h 10m

Nashville Intl

Mon 9/29

5:25 am-7:00 am

Nonstop1h 35m

$87

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 10/6

9:30 am-1:10 pm

1 stop3h 40m

Nashville Intl

Thu 10/9

1:35 pm-3:10 pm

Nonstop1h 35m

$87

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 11/4

7:30 am-11:50 am

1 stop4h 20m

Nashville Intl

Sat 11/8

5:40 am-7:20 am

Nonstop1h 40m

$87

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 10/28

12:40 pm-5:30 pm

1 stop4h 50m

Nashville Intl

Tue 11/4

6:35 pm-8:15 pm

Nonstop1h 40m

$87

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 10/18

6:30 am-11:35 am

1 stop5h 05m

Nashville Intl

Thu 10/23

1:35 pm-3:10 pm

Nonstop1h 35m

$87

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
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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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kentucky (average of $299). Flying from Chicago Midway Airport to Kentucky in April is currently the most expensive (average of $369). 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 August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Kentucky as you normally would.

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 August 14, 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
4,244 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Kentucky one-way?

    One-way options have recently been found by users for as low as $39 on Southwest. Other airlines that offer cheap prices include Allegiant Air from $53 and Frontier from $72 one-way.

  • 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 - Lexington Blue Grass, Chicago Midway - Nashville Intl is the most popular route from Chicago Midway Airport to Kentucky.

  • What are the cheapest flights from Chicago Midway Airport to Kentucky?

    Looking at all options, your cheapest flight can be booked for $38. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $77 on average our data indicates $237 when flying 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kentucky (average of $299). Flying from Chicago Midway Airport to Kentucky in April is currently the most expensive (average of $369). 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

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Alternative routes for Midway to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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O'Hare Intl to Cleveland 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$124Average$532FlexibilityNo cancel feeOn-time63%

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