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Midway

$39+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$77
(Southwest)

One-way from

$39
(Southwest)

Popular in

March

Cheapest in

August

Average price

$253

Good round-trip deal

$304 or less

Good one-way deal

$167 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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Highest demand for flights based on searches. 5% potential increase in price ($14 potential increase over avg. RT price).
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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 April 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 April 24, 2025.

This Southwest deal was found by Cheapflights users on 4/23. 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 5/143:35 pmBNA - MDW
1 stop4h 20mSouthwest
Tue 5/208:15 amMDW - BNA
Nonstop1h 30mSouthwest
Deal found 4/23$87
This Southwest deal was found by Cheapflights users on 4/22. 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 5/146:25 amSDF - MDW
Nonstop1h 15mSouthwest
Sat 5/176:40 amMDW - SDF
1 stop6h 20mSouthwest
Deal found 4/22$124
This Southwest deal was found by Cheapflights users on 4/22. 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 6/76:40 pmCVG - MDW
Nonstop1h 10mSouthwest
Tue 6/106:10 pmMDW - CVG
1 stop4h 10mSouthwest
Deal found 4/22$124
This Frontier deal was found by Cheapflights users on 4/23. 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.
Thu 5/155:45 amCVG - MDW
1 stop7h 39mFrontier
Fri 5/161:19 pmMDW - CVG
1 stop10h 40mFrontier
Deal found 4/23$160
This Delta deal was found by Cheapflights users on 4/23. 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 6/123:00 pmCVG - MDW
1 stop4h 41mDelta
Mon 6/166:47 pmMDW - CVG
1 stop4h 30mDelta
Deal found 4/23$176
This Delta deal was found by Cheapflights users on 4/22. 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 6/257:06 amSDF - MDW
1 stop5h 53mDelta
Mon 6/301:09 pmMDW - SDF
1 stop5h 53mDelta
Deal found 4/22$177
This Delta deal was found by Cheapflights users on 4/23. 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 6/185:15 amBNA - MDW
1 stop4h 26mDelta
Tue 6/246:20 pmMDW - BNA
1 stop3h 38mDelta
Deal found 4/23$177
This Frontier deal was found by Cheapflights users on 4/23. 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 5/309:59 amBNA - MDW
1 stop10h 18mFrontier
Sun 6/19:12 pmMDW - BNA
1 stop11h 56mFrontier
Deal found 4/23$198
This Delta deal was found by Cheapflights users on 4/23. 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.
Fri 6/67:50 amTYS - MDW
1 stop5h 38mDelta
Mon 6/166:47 pmMDW - TYS
1 stop4h 12mDelta
Deal found 4/23$209
This Delta deal was found by Cheapflights users on 4/22. 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 5/145:55 pmLEX - MDW
1 stop4h 33mDelta
Sat 5/311:08 pmMDW - LEX
1 stop3h 22mDelta
Deal found 4/22$214
This Mytrip deal was found by Cheapflights users on 4/23. 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.
Sun 6/17:30 amTYS - MDW
2 stops36h 44mAllegiant Air
Fri 6/62:53 pmMDW - TYS
Nonstop1h 25mAllegiant Air
Deal found 4/23$223
This Delta deal was found by Cheapflights users on 4/23. 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 5/2810:26 amTRI - MDW
1 stop5h 54mDelta
Sun 6/16:00 amMDW - TRI
1 stop5h 55mDelta
Deal found 4/23$239

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 April 24, 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 5/15

5:15 am-6:50 am

Nonstop1h 35m

Chicago Midway

Mon 5/19

8:30 pm-10:00 pm

Nonstop1h 30m

$77

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 5/14

6:25 am-6:40 am

Nonstop1h 15m

Chicago Midway

Sat 5/17

6:40 am-2:00 pm

1 stop6h 20m

$124

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 6/7

6:40 pm-6:50 pm

Nonstop1h 10m

Chicago Midway

Tue 6/10

6:10 pm-11:20 pm

1 stop4h 10m

$124

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 5/15

5:45 am-12:24 pm

1 stop7h 39m

Chicago Midway

Fri 5/16

1:19 pm-12:59 am

1 stop10h 40m

$160

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 6/12

3:00 pm-6:41 pm

1 stop4h 41m

Chicago Midway

Mon 6/16

6:47 pm-12:17 am

1 stop4h 30m

$176

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 6/25

7:06 am-11:59 am

1 stop5h 53m

Chicago Midway

Thu 7/3

1:09 pm-8:02 pm

1 stop5h 53m

$177

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 6/21

6:05 am-12:29 pm

1 stop6h 24m

Chicago Midway

Mon 6/23

6:20 pm-9:58 pm

1 stop3h 38m

$178

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Fri 6/6

7:50 am-12:28 pm

1 stop5h 38m

Chicago Midway

Mon 6/16

6:47 pm-11:59 pm

1 stop4h 12m

$209

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 5/1

7:45 pm-7:08 pm

1 stop23h 23m

Chicago Midway

Sun 5/4

10:55 am-9:09 am

1 stop22h 14m

$211

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Fri 5/9

3:44 pm-9:28 pm

1 stop6h 44m

Chicago Midway

Sun 5/11

6:00 am-12:19 pm

1 stop5h 19m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 36 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 April 24, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 24, 2025.
Read through reviews of airlines operating flights from Kentucky to Chicago, such as Southwest, Delta and Allegiant Air. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,283 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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 $39 on Southwest. Other airlines that offer cheap prices include Allegiant Air from $49 and Delta from $89 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 $100. While the most popular route (Cincinnati Cinci./N. Kentucky - Chicago Midway) can be booked for $77 on average our data indicates $301 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 Kentucky?

Book flights to Kentucky if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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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Oakland to O'Hare Intl flights
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Los Angeles to Midway flights
Tampa to O'Hare Intl flights
Philadelphia to Midway flights
Cleveland to O'Hare Intl flights
Minneapolis to Midway flights
Baltimore to Midway flights
Hobby to Midway flights
Seattle to Midway flights
Denver to Midway flights
Love Field to O'Hare Intl flights

Top 2 airlines flying from Kentucky to Midway

Discover the top 2 airlines 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$135Average$365FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$172Average$275FlexibilityNo cancel feeOn-time63%

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