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Midway

$67+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Jan 28 — Feb 41
Wed 1/28
Wed 2/4
1 adult, Economy
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Cheap 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 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.
Mon 12/296:00 amTYS - MDW
1 stop4h 05mDelta
Sat 1/36:00 amMDW - TYS
1 stop6h 42mDelta
Deal found 12/27$349
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 12/295:52 pmLEX - MDW
1 stop5h 30mDelta
Fri 1/25:05 pmMDW - LEX
1 stop5h 54mDelta
Deal found 12/28$383
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.
Tue 12/305:52 pmLEX - MDW
1 stop5h 30mDelta
Fri 1/29:50 amMDW - LEX
1 stop6h 07mDelta
Deal found 12/27$411
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:02 pmBNA - MDW
1 stop24h 53mFrontier
Sun 1/410:50 pmMDW - BNA
1 stop19h 17mFrontier
Deal found 12/27$463
This Frontier deal was found by Cheapflights users on 12/26. 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.
Tue 12/302:50 pmCVG - MDW
1 stop8h 22mFrontier
Wed 12/313:10 pmMDW - CVG
1 stop8h 56mFrontier
Deal found 12/26$467
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 12/316:27 amTYS - MDW
1 stop5h 39mDelta
Sun 1/46:00 amMDW - TYS
1 stop4h 09mDelta
Deal found 12/28$469
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 12/314:54 pmTYS - MDW
1 stop6h 28mDelta
Sat 1/36:00 amMDW - TYS
1 stop6h 42mDelta
Deal found 12/28$484
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 12/314:54 pmTYS - MDW
1 stop6h 28mDelta
Fri 1/26:00 amMDW - TYS
1 stop4h 09mDelta
Deal found 12/28$519
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.
Tue 12/305:50 amCVG - MDW
1 stop5h 35mSouthwest
Sun 1/116:10 pmMDW - CVG
Nonstop1h 10mSouthwest
Deal found 12/27$521
This Delta deal was found by Cheapflights users on 12/26. 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 12/316:27 amTYS - MDW
1 stop5h 39mDelta
Thu 1/16:00 amMDW - TYS
1 stop6h 20mDelta
Deal found 12/26$549
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.
Mon 12/298:20 pmBNA - MDW
Nonstop1h 35mSouthwest
Sun 1/254:55 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 12/27$561
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 12/286:59 pmTYS - MDW
1 stop4h 23mDelta
Wed 12/319:50 amMDW - TYS
1 stop5h 24mDelta
Deal found 12/27$567

Find flight deals from Kentucky to Midway

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$133
(Southwest)

One-way from

$67
(Southwest)

Popular in

March

Cheapest in

November

Average price

$275

Good round-trip deal

$326 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
Search Deals
From Kentucky to Chicago Midway
Search Deals
One-way flight from Kentucky to Chicago Midway
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($0 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Kentucky to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Kentucky to Chicago Midway.
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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 December 29, 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

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 1/27

6:30 pm-6:45 pm

Nonstop1h 15m

Chicago Midway

Tue 2/3

10:00 am-12:15 pm

Nonstop1h 15m

$133

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 1/17

6:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Tue 1/20

10:00 am-12:15 pm

Nonstop1h 15m

$138

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 2/7

6:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Mon 2/9

9:55 am-12:10 pm

Nonstop1h 15m

$157

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 2/12

8:51 pm-2:26 pm

1 stop17h 35m

Chicago Midway

Thu 2/19

7:30 am-8:06 pm

1 stop12h 36m

$163

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Mon 1/26

6:45 am-7:10 am

Nonstop1h 25m

Chicago Midway

Mon 2/2

10:00 am-12:15 pm

Nonstop1h 15m

$171

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 1/17

7:50 am-12:48 pm

1 stop5h 58m

Chicago Midway

Tue 1/20

9:50 am-4:19 pm

1 stop5h 29m

$176

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 2/11

6:23 am-1:06 pm

1 stop7h 43m

Chicago Midway

Sat 2/14

11:45 am-9:14 pm

2 stops8h 29m

$179

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 4/23

5:20 am-6:55 am

Nonstop1h 35m

Chicago Midway

Mon 4/27

9:35 pm-11:00 pm

Nonstop1h 25m

$191

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 1/17

6:20 pm-6:30 pm

Nonstop1h 10m

Chicago Midway

Sun 1/18

5:30 pm-7:40 pm

Nonstop1h 10m

$193

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 2/19

8:51 pm-2:26 pm

1 stop17h 35m

Chicago Midway

Sun 2/22

7:30 am-1:40 pm

1 stop6h 10m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

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, September is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $77). Flying from Kentucky to Chicago Midway Airport in February is currently the most expensive (average of $338). 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 December 29, 2025.

It’s optimal to fly from Kentucky to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Midway. Price data was last updated on December 16, 2024.

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

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, Frontier, and Delta can get you from Kentucky to Chicago Midway Airport in just under 1h 15m. Your travel time can differ by up to 16h 20m. The distance between Kentucky and Chicago Midway Airport is about 271 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $134. While the most popular route (Cincinnati Cinci./N. Kentucky - Chicago Midway) can be booked for $186 on average, our data indicates $354 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, September is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $77). Flying from Kentucky to Chicago Midway Airport in February is currently the most expensive (average of $338). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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Fort Lauderdale to Midway flights

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 December 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$259FlexibilityNo cancel feeOn-time63%

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