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$49+ Cheap flights from Kentucky to Midway (MDW)

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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Kentucky to Midway

Keep the following information in mind while searching for Kentucky to Midway flight deals. Data was last updated September 16, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

April

Average price

$275

Good round-trip deal

$238 or less

Good one-way deal

$178 or less
From Kentucky to Chicago Midway
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One-way flight from Kentucky to Chicago Midway
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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($3 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 Kentucky to Chicago Midway.
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Price to beat on a one-way flight from Kentucky to Chicago Midway.
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Find flight deals from Kentucky to Midway

Cheapest flights from Kentucky to Midway
Explore the most affordable flight options available from Kentucky to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 10/95:30 amBNA - MDW
Nonstop1h 35mSouthwest
Mon 10/139:30 pmMDW - BNA
Nonstop1h 25mSouthwest
Deal found 9/15$97
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 9/196:24 pmTYS - MDW
Nonstop1h 36mAllegiant Air
Mon 9/227:50 pmMDW - TYS
Nonstop1h 31mAllegiant Air
Deal found 9/15$98
This Booking.com deal was found by Cheapflights users on 9/15. 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 9/226:24 pmTYS - MDW
Nonstop1h 36mAllegiant Air
Fri 9/267:50 pmMDW - TYS
Nonstop1h 31mAllegiant Air
Deal found 9/15$103
This Southwest deal was found by Cheapflights users on 9/15. 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 11/191:10 pmBNA - MDW
1 stop3h 25mSouthwest
Sat 11/225:35 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 9/15$103
This Booking.com deal was found by Cheapflights users on 9/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/241:23 pmTYS - MDW
Nonstop1h 32mAllegiant Air
Mon 10/278:24 pmMDW - TYS
Nonstop1h 24mAllegiant Air
Deal found 9/14$105
This Southwest deal was found by Cheapflights users on 9/16. 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 11/43:20 pmSDF - MDW
1 stop6h 45mSouthwest
Thu 11/67:15 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 9/16$107
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 9/196:24 pmTYS - MDW
Nonstop1h 36mAllegiant Air
Mon 9/293:16 pmMDW - TYS
Nonstop1h 31mAllegiant Air
Deal found 9/15$110
This Southwest deal was found by Cheapflights users on 9/14. 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.
Wed 10/151:50 pmBNA - MDW
1 stop3h 15mSouthwest
Sat 10/1811:00 amMDW - BNA
1 stop4h 40mSouthwest
Deal found 9/14$112
This Southwest deal was found by Cheapflights users on 9/14. 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.
Tue 10/1411:55 amSDF - MDW
Nonstop1h 15mSouthwest
Tue 10/2112:30 pmMDW - SDF
1 stop8h 10mSouthwest
Deal found 9/14$113
This Mytrip deal was found by Cheapflights users on 9/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:44 pmTYS - MDW
Nonstop1h 32mAllegiant Air
Fri 11/72:57 pmMDW - TYS
Nonstop1h 25mAllegiant Air
Deal found 9/16$113
This Booking.com deal was found by Cheapflights users on 9/14. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/291:50 pmTYS - MDW
Nonstop1h 36mAllegiant Air
Fri 10/312:06 pmMDW - TYS
Nonstop1h 24mAllegiant Air
Deal found 9/14$116
This Southwest deal was found by Cheapflights users on 9/15. 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 10/167:00 pmBNA - MDW
1 stop5h 25mSouthwest
Thu 10/239:40 amMDW - BNA
1 stop4h 20mSouthwest
Deal found 9/15$117

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Midway 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 16, 2025.
Use the filters below to find and compare flights from Kentucky to Chicago Midway Airport that are best for you.

Fly from

Kentucky

Fly to

Midway

Route

Depart

Return

Price

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 10/23

7:30 am-9:05 am

Nonstop1h 35m

Chicago Midway

Sat 10/25

7:20 pm-8:45 pm

Nonstop1h 25m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 11/8

5:40 am-7:20 am

Nonstop1h 40m

Chicago Midway

Mon 11/10

9:35 pm-11:00 pm

Nonstop1h 25m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 10/11

3:15 pm-4:50 pm

Nonstop1h 35m

Chicago Midway

Mon 10/13

9:30 pm-10:55 pm

Nonstop1h 25m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Mon 10/20

9:45 pm-11:15 pm

Nonstop1h 30m

Chicago Midway

Tue 10/21

4:10 pm-5:35 pm

Nonstop1h 25m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 11/19

1:10 pm-4:35 pm

1 stop3h 25m

Chicago Midway

Sat 11/22

5:35 pm-7:05 pm

Nonstop1h 30m

$103

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 10/15

7:05 am-8:40 am

Nonstop1h 35m

Chicago Midway

Wed 10/15

12:40 pm-5:30 pm

1 stop4h 50m

$107

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 10/15

8:50 pm-10:25 pm

Nonstop1h 35m

Chicago Midway

Sat 10/18

12:50 pm-6:20 pm

1 stop5h 30m

$107

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Mon 11/3

12:10 pm-5:10 pm

2 stops5h 00m

Chicago Midway

Mon 11/10

9:35 pm-11:00 pm

Nonstop1h 25m

$112

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 11/20

3:20 pm-9:05 pm

1 stop6h 45m

Chicago Midway

Sat 11/22

7:55 am-7:00 pm

2 stops10h 05m

$122

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 10/24

5:59 pm-5:13 pm

1 stop24h 14m

Chicago Midway

Mon 10/27

8:24 pm-10:48 pm

Nonstop1h 24m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
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Best time to book a flight from Kentucky to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Kentucky 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 Kentucky to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $160). Flying from Kentucky to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 KY to MDW?

Find hourly flight availability from Kentucky to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Kentucky to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Midway. 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 Kentucky to Chicago Midway Airport?

    Southwest, Delta, and Frontier can get you from Kentucky to Chicago Midway Airport in just under 1h 35m. Your travel time can differ by up to 10h 28m. The distance between Kentucky and Chicago Midway Airport is about 395 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    One-way options have recently been found by users for as low as $49 on Southwest. Other airlines that offer cheap prices include Allegiant Air from $55 and Frontier from $72 one-way.

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

    When deciding which route to take from Kentucky to Chicago Midway Airport consider Cincinnati Cinci./N. Kentucky - Chicago Midway, Nashville Intl - Chicago Midway or Knoxville McGhee Tyson - Chicago Midway as they are the most popular.

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

    Looking at all options, your cheapest flight can be booked for $48. While the most popular route (Cincinnati Cinci./N. Kentucky - Chicago Midway) can be booked for $153 on average, our data indicates $263 when flying from Kentucky to Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kentucky to Midway 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 Kentucky to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $160). Flying from Kentucky to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Kentucky to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Kentucky to Midway

Discover the top airline that operate flights from Kentucky to Midway. 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$260FlexibilityNo cancel feeOn-time63%

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