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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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Southwest)

One-way from

$39
(Southwest)

Popular in

February

Cheapest in

August

Average price

$255

Good round-trip deal

$129 or less
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
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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 ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip 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 September 29, 2025.

This Southwest deal was found by Cheapflights users on 9/29. 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 12/258:50 amMDW - BNA
Nonstop1h 30mSouthwest
Thu 1/19:00 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 9/29$97
This Southwest deal was found by Cheapflights users on 9/29. 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 11/62:20 pmMDW - SDF
1 stop8h 55mSouthwest
Mon 11/104:45 pmSDF - MDW
1 stop7h 15mSouthwest
Deal found 9/29$102
This Southwest deal was found by Cheapflights users on 9/27. 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.
Fri 10/317:05 pmMDW - BNA
Nonstop1h 25mSouthwest
Sat 11/17:15 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 9/27$118
This Southwest deal was found by Cheapflights users on 9/28. 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.
Fri 10/317:05 pmMDW - BNA
Nonstop1h 25mSouthwest
Sun 11/25:40 amBNA - MDW
Nonstop1h 40mSouthwest
Deal found 9/28$127
This Cheapflightsfares deal was found by Cheapflights users on 9/29. 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.
Mon 10/612:08 pmMDW - TYS
Nonstop1h 24mAllegiant Air
Fri 10/1010:44 amTYS - MDW
Nonstop1h 32mAllegiant Air
Deal found 9/29$138
This Southwest deal was found by Cheapflights users on 9/27. 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.
Sat 11/13:50 pmMDW - BNA
Nonstop1h 25mSouthwest
Sat 11/17:15 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 9/27$139
This Southwest deal was found by Cheapflights users on 9/28. 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.
Thu 10/305:20 pmMDW - BNA
1 stop4h 55mSouthwest
Fri 10/316:30 amBNA - MDW
1 stop5h 15mSouthwest
Deal found 9/28$147
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:11 pmMDW - BNA
1 stop11h 48mFrontier
Mon 10/271:53 pmBNA - MDW
1 stop9h 10mFrontier
Deal found 9/29$148
This Trip.com deal was found by Cheapflights users on 9/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/312:06 pmMDW - TYS
Nonstop1h 24mAllegiant Air
Mon 10/2010:46 amTYS - MDW
Nonstop1h 32mAllegiant Air
Deal found 9/28$148
This Booking.com deal was found by Cheapflights users on 9/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3010:12 amMDW - BNA
1 stop24h 03mFrontier
Mon 11/310:02 amBNA - MDW
1 stop7h 47mFrontier
Deal found 9/27$150
This Booking.com deal was found by Cheapflights users on 9/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/293:16 pmMDW - TYS
Nonstop1h 31mAllegiant Air
Mon 10/610:46 amTYS - MDW
Nonstop1h 32mAllegiant Air
Deal found 9/27$153
This Southwest deal was found by Cheapflights users on 9/28. 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 10/218:35 pmMDW - SDF
Nonstop1h 10mSouthwest
Sat 10/254:25 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 9/28$154

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 September 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

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 11/6

2:20 pm-12:15 am

1 stop8h 55m

Louisville Intl

Mon 11/10

12:25 pm-8:35 pm

2 stops9h 10m

$108

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 10/31

12:55 pm-6:25 pm

1 stop5h 30m

Nashville Intl

Sun 11/2

5:40 am-7:20 am

Nonstop1h 40m

$137

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 11/8

5:50 am-7:20 am

Nonstop1h 30m

Nashville Intl

Sat 11/8

10:00 am-11:45 am

Nonstop1h 45m

$139

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 10/30

5:20 pm-10:15 pm

1 stop4h 55m

Nashville Intl

Fri 10/31

6:30 am-11:45 am

1 stop5h 15m

$147

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 11/14

9:55 pm-11:20 pm

Nonstop1h 25m

Nashville Intl

Sat 11/15

5:25 am-7:05 am

Nonstop1h 40m

$148

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 12/9

12:25 pm-1:55 pm

Nonstop1h 30m

Nashville Intl

Fri 12/12

9:55 pm-11:30 pm

Nonstop1h 35m

$148

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 10/21

8:35 pm-10:45 pm

Nonstop1h 10m

Louisville Intl

Sat 10/25

4:25 pm-4:40 pm

Nonstop1h 15m

$154

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Sat 10/25

12:55 pm-3:05 pm

Nonstop1h 10m

Louisville Intl

Mon 10/27

6:15 am-6:30 am

Nonstop1h 15m

$154

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 10/30

6:00 am-7:25 am

Nonstop1h 25m

Nashville Intl

Sun 11/2

5:40 am-7:20 am

Nonstop1h 40m

$157

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 11/7

9:55 pm-11:20 pm

Nonstop1h 25m

Nashville Intl

Mon 11/10

9:55 pm-11:30 pm

Nonstop1h 35m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

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 September 29, 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 September 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
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 5h 44m. Fly via Southwest, Allegiant Air, or Frontier to get the fastest option. Chicago Midway Airport and Kentucky are separated by a distance of 249 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.

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

    Looking at all options, your cheapest flight can be booked for $97. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $127 on average, our data indicates $196 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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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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$124Average$556FlexibilityNo cancel feeOn-time63%

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