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$49+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Southwest deal was found by Cheapflights users on 11/11. 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.
Tue 12/912:25 pmMDW - BNA
Nonstop1h 30mSouthwest
Tue 12/162:20 pmBNA - MDW
Nonstop1h 40mSouthwest
Deal found 11/11$117
This Southwest deal was found by Cheapflights users on 11/12. 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.
Wed 12/109:50 amMDW - BNA
1 stop5h 10mSouthwest
Wed 12/171:10 pmBNA - MDW
1 stop3h 25mSouthwest
Deal found 11/12$132
This Southwest deal was found by Cheapflights users on 11/13. 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 12/1312:00 pmMDW - BNA
Nonstop1h 25mSouthwest
Wed 12/1711:05 amBNA - MDW
Nonstop1h 40mSouthwest
Deal found 11/13$137
This Southwest deal was found by Cheapflights users on 11/12. 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.
Wed 12/312:25 pmMDW - BNA
Nonstop1h 30mSouthwest
Sat 12/610:00 amBNA - MDW
Nonstop1h 45mSouthwest
Deal found 11/12$144
This Southwest deal was found by Cheapflights users on 11/12. 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.
Wed 12/108:50 pmMDW - SDF
Nonstop1h 15mSouthwest
Thu 12/111:50 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 11/12$144
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Sun 12/146:15 amMDW - CVG
1 stop27h 28mFrontier
Sun 1/119:20 pmCVG - MDW
1 stop26h 39mFrontier
Deal found 11/13$147
This Southwest deal was found by Cheapflights users on 11/12. 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.
Sun 12/149:30 amMDW - BNA
1 stop2h 45mSouthwest
Tue 12/161:10 pmBNA - MDW
1 stop3h 25mSouthwest
Deal found 11/12$148
This Southwest deal was found by Cheapflights users on 11/12. 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 12/68:25 amMDW - BNA
1 stop3h 25mSouthwest
Wed 12/1011:05 amBNA - MDW
Nonstop1h 40mSouthwest
Deal found 11/12$150
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Thu 12/47:23 pmMDW - CVG
1 stop20h 00mFrontier
Mon 12/811:53 amCVG - MDW
1 stop21h 53mFrontier
Deal found 11/13$165
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/212:11 pmMDW - TYS
Nonstop1h 25mMultiple Airlines
Sun 11/235:49 pmTYS - MDW
1 stop24h 26mMultiple Airlines
Deal found 11/12$166
This Southwest deal was found by Cheapflights users on 11/12. 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 12/239:30 amMDW - SDF
Nonstop1h 15mSouthwest
Thu 1/11:50 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 11/12$176
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Thu 12/117:23 pmMDW - CVG
1 stop20h 00mFrontier
Thu 12/182:50 pmCVG - MDW
1 stop8h 22mFrontier
Deal found 11/13$182

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

August

Average price

$275

Good round-trip deal

$263 or less

Good one-way deal

$147 or less
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. 15% potential increase in price ($55 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 November 2025
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Kentucky.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Kentucky.
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 November 13, 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

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 12/9

12:25 pm-1:55 pm

Nonstop1h 30m

Nashville Intl

Tue 12/16

2:20 pm-4:00 pm

Nonstop1h 40m

$117

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 12/10

5:35 am-7:05 am

Nonstop1h 30m

Nashville Intl

Wed 12/17

1:10 pm-4:35 pm

1 stop3h 25m

$123

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 1/1

2:25 pm-4:35 pm

Nonstop1h 10m

Louisville Intl

Mon 1/5

8:10 pm-8:30 pm

Nonstop1h 20m

$134

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sun 12/14

6:20 am-7:50 am

Nonstop1h 30m

Nashville Intl

Tue 12/16

11:05 am-12:45 pm

Nonstop1h 40m

$137

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 12/3

12:25 pm-1:55 pm

Nonstop1h 30m

Nashville Intl

Sat 12/6

10:00 am-11:45 am

Nonstop1h 45m

$144

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 12/10

8:50 pm-11:05 pm

Nonstop1h 15m

Louisville Intl

Thu 12/11

1:50 pm-2:05 pm

Nonstop1h 15m

$144

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 12/12

9:55 pm-11:20 pm

Nonstop1h 25m

Nashville Intl

Sun 12/14

5:30 am-7:10 am

Nonstop1h 40m

$157

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 12/4

7:23 pm-4:23 pm

1 stop20h 00m

Cincinnati Cinci./N. Kentucky

Mon 12/8

11:53 am-8:46 am

1 stop21h 53m

$170

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 1/1

6:00 am-1:35 pm

1 stop6h 35m

Louisville Intl

Mon 1/5

12:36 pm-4:31 pm

1 stop4h 55m

$174

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 12/23

9:30 am-11:45 am

Nonstop1h 15m

Louisville Intl

Thu 1/1

1:50 pm-2:05 pm

Nonstop1h 15m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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, 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 November 13, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 15% on flights from Chicago Midway Airport to Kentucky by exploring options for tickets at noon.

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 16, 2024.

Travelers seeking maximum savings on their Chicago Midway Airport to Kentucky flight should consider departing on Saturday mornings 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 November 13, 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
4,242 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

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 1h 30m. Fly via Southwest, Frontier, 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 - Louisville Intl, 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 $117 on average, our data indicates $362 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, 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

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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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$129Average$511FlexibilityNo cancel feeOn-time63%

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