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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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

November

Average price

$255

Good round-trip deal

$326 or less

Good one-way deal

$169 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
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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, 1% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/29. 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 12/46:45 amSDF - MDW
Nonstop1h 15mSouthwest
Mon 12/810:05 amMDW - SDF
Nonstop1h 25mSouthwest
Deal found 10/29$97
This Southwest deal was found by Cheapflights users on 10/29. 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 12/48:10 amBNA - MDW
Nonstop1h 45mSouthwest
Mon 12/812:25 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 10/29$97
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sat 12/65:25 amBNA - MDW
Nonstop1h 40mSouthwest
Tue 12/98:50 amMDW - BNA
Nonstop1h 30mSouthwest
Deal found 10/29$127
This Southwest deal was found by Cheapflights users on 10/28. 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.
Sat 12/67:10 amSDF - MDW
Nonstop1h 20mSouthwest
Mon 12/88:50 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 10/28$134
This Booking.com deal was found by Cheapflights users on 10/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:42 pmBNA - MDW
1 stop19h 48mFrontier
Sun 11/168:32 amMDW - BNA
1 stop5h 07mFrontier
Deal found 10/29$144
This Southwest deal was found by Cheapflights users on 10/29. 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.
Sat 12/61:50 pmBNA - MDW
1 stop4h 40mSouthwest
Wed 12/101:20 pmMDW - BNA
1 stop5h 55mSouthwest
Deal found 10/29$147
This Booking.com deal was found by Cheapflights users on 10/30. 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 11/69:11 amBNA - MDW
1 stop5h 22mFrontier
Thu 11/1310:12 amMDW - BNA
1 stop26h 07mFrontier
Deal found 10/30$152
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:15 amSDF - MDW
1 stop5h 40mDelta
Mon 12/85:29 pmMDW - SDF
1 stop4h 29mDelta
Deal found 10/29$157
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amBNA - MDW
1 stop6h 34mDelta
Tue 1/65:31 pmMDW - BNA
1 stop5h 29mDelta
Deal found 10/29$157
This Southwest deal was found by Cheapflights users on 10/29. 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.
Fri 12/58:55 pmBNA - MDW
Nonstop1h 40mSouthwest
Sun 12/79:30 amMDW - BNA
1 stop2h 45mSouthwest
Deal found 10/29$163
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/242:22 pmSDF - MDW
1 stop4h 46mDelta
Tue 12/161:14 pmMDW - SDF
1 stop3h 22mDelta
Deal found 10/29$167
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:15 amBNA - MDW
1 stop6h 40mDelta
Sun 12/76:00 amMDW - BNA
1 stop3h 57mDelta
Deal found 10/29$167

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 October 30, 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 12/4

8:55 pm-10:35 pm

Nonstop1h 40m

Chicago Midway

Mon 12/8

5:35 am-7:05 am

Nonstop1h 30m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Mon 12/8

8:55 pm-10:35 pm

Nonstop1h 40m

Chicago Midway

Thu 1/1

6:35 am-8:05 am

Nonstop1h 30m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 12/9

8:55 pm-10:35 pm

Nonstop1h 40m

Chicago Midway

Thu 12/11

8:30 pm-10:00 pm

Nonstop1h 30m

$97

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 12/4

11:45 am-8:45 pm

2 stops10h 00m

Chicago Midway

Mon 12/8

10:05 am-12:30 pm

Nonstop1h 25m

$112

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 12/6

5:25 am-7:05 am

Nonstop1h 40m

Chicago Midway

Tue 12/9

8:50 am-10:20 am

Nonstop1h 30m

$127

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 12/6

5:25 pm-7:05 pm

Nonstop1h 40m

Chicago Midway

Wed 12/10

5:35 am-7:05 am

Nonstop1h 30m

$127

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 12/6

7:10 am-7:30 am

Nonstop1h 20m

Chicago Midway

Mon 12/8

8:50 pm-11:05 pm

Nonstop1h 15m

$134

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 12/5

6:35 pm-8:15 pm

Nonstop1h 40m

Chicago Midway

Tue 12/9

3:30 pm-7:55 pm

1 stop4h 25m

$137

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 12/23

5:35 pm-11:05 pm

1 stop6h 30m

Chicago Midway

Tue 12/30

9:30 am-11:45 am

Nonstop1h 15m

$144

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/3

6:16 pm-11:47 pm

1 stop6h 31m

Chicago Midway

Tue 12/9

5:29 pm-11:59 pm

1 stop5h 30m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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, January is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $73). Flying from Kentucky to Chicago Midway Airport in February is currently the most expensive (average of $282). 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 October 30, 2025.

It’s optimal to fly from Kentucky to Chicago Midway Airport in the afternoon. By choosing this option you can save up to 39% on the cost of your flight, compared to a flight in the evening.

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. Monday afternoons 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 40m. Your travel time can differ by up to 9h 33m. 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 $66 and Frontier from $95 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 Nashville Intl - Chicago Midway, Cincinnati Cinci./N. Kentucky - 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 $137. While the most popular route (Nashville Intl - Chicago Midway) can be booked for $97 on average, our data indicates $355 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, January is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $73). Flying from Kentucky to Chicago Midway Airport in February is currently the most expensive (average of $282). 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
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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John F Kennedy Intl to Midway flights
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Dallas/Fort Worth to Midway flights
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Hobby to Midway flights
Atlanta to Midway flights
LaGuardia to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Denver to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Reagan-National to Midway flights
Austin to O'Hare Intl flights
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Love Field to O'Hare Intl flights
Hartford to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
Boston to Midway flights
Providence to O'Hare Intl flights
Sacramento to O'Hare Intl flights
Columbus to O'Hare Intl 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$253FlexibilityNo cancel feeOn-time63%

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