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Midway

$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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$82
(Cheapflightsfares)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

April

Average price

$280

Good round-trip deal

$228 or less

Good one-way deal

$206 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, 0% 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 July 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 julio 31, 2025.

This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/41:23 pmTYS - MDW
Nonstop1h 33mAllegiant Air
vie. 8/82:46 pmMDW - TYS
Nonstop1h 26mAllegiant Air
Deal found 7/30$79
This Southwest deal was found by Cheapflights users on 7/31. 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.
sáb. 8/306:35 amSDF - MDW
Nonstop1h 15mSouthwest
lun. 9/88:35 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 7/31$97
This Southwest deal was found by Cheapflights users on 7/31. 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.
jue. 8/218:20 amBNA - MDW
Nonstop1h 40mSouthwest
lun. 8/257:55 amMDW - BNA
Nonstop1h 30mSouthwest
Deal found 7/31$97
This Delta deal was found by Cheapflights users on 7/29. 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.
mar. 9/166:00 amSDF - MDW
1 stop4h 40mDelta
sáb. 9/206:15 pmMDW - SDF
1 stop3h 29mDelta
Deal found 7/29$177
This Southwest deal was found by Cheapflights users on 7/31. 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.
jue. 8/216:40 amCVG - MDW
Nonstop1h 10mSouthwest
lun. 8/256:45 pmMDW - CVG
Nonstop1h 10mSouthwest
Deal found 7/31$177
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/2910:30 amCVG - MDW
1 stop12h 18mFrontier
dom. 8/316:15 amMDW - CVG
1 stop10h 19mFrontier
Deal found 7/30$178
This Trip.com deal was found by Cheapflights users on 7/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/81:23 pmTYS - MDW
Nonstop1h 33mMultiple Airlines
sáb. 8/92:44 pmMDW - TYS
1 stop24h 45mMultiple Airlines
Deal found 7/29$181
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/97:00 amBNA - MDW
1 stop13h 54mFrontier
vie. 8/1512:35 pmMDW - BNA
1 stop11h 26mFrontier
Deal found 7/28$188
This Delta deal was found by Cheapflights users on 7/31. 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.
sáb. 8/308:00 amCVG - MDW
1 stop5h 28mDelta
sáb. 8/306:17 pmMDW - CVG
1 stop3h 49mDelta
Deal found 7/31$197
This Delta deal was found by Cheapflights users on 7/31. 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.
mié. 8/206:25 amBNA - MDW
1 stop6h 03mDelta
sáb. 8/236:04 amMDW - BNA
1 stop5h 49mDelta
Deal found 7/31$208
This Delta deal was found by Cheapflights users on 7/29. 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.
mar. 8/266:00 amLEX - MDW
1 stop4h 36mDelta
mar. 9/26:17 pmMDW - LEX
1 stop3h 19mDelta
Deal found 7/29$209
This Delta deal was found by Cheapflights users on 7/29. 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.
vie. 9/126:08 pmTYS - MDW
1 stop4h 28mDelta
lun. 9/156:00 amMDW - TYS
1 stop6h 07mDelta
Deal found 7/29$209

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 julio 31, 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

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

vie. 8/22

2:29 pm-3:02 pm

Nonstop1h 33m

Chicago Midway

lun. 8/25

3:52 pm-6:20 pm

Nonstop1h 28m

$82

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

sáb. 8/30

6:35 am-6:50 am

Nonstop1h 15m

Chicago Midway

lun. 9/8

8:35 pm-10:50 pm

Nonstop1h 15m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

jue. 8/21

4:25 pm-6:05 pm

Nonstop1h 40m

Chicago Midway

lun. 8/25

12:00 pm-1:25 pm

Nonstop1h 25m

$97

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 9/16

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

sáb. 9/20

6:15 pm-10:44 pm

1 stop3h 29m

$177

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

jue. 8/21

6:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

lun. 8/25

6:45 pm-8:55 pm

Nonstop1h 10m

$177

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

vie. 8/29

10:30 am-9:48 pm

1 stop12h 18m

Chicago Midway

dom. 8/31

6:15 am-5:34 pm

1 stop10h 19m

$178

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

jue. 8/14

5:25 pm-11:41 am

1 stop19h 16m

Chicago Midway

vie. 8/22

3:52 pm-6:20 pm

Nonstop1h 28m

$182

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

sáb. 8/9

7:00 am-8:54 pm

1 stop13h 54m

Chicago Midway

vie. 8/15

12:35 pm-12:01 am

1 stop11h 26m

$188

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

sáb. 8/30

8:00 am-12:28 pm

1 stop5h 28m

Chicago Midway

sáb. 8/30

6:17 pm-11:06 pm

1 stop3h 49m

$197

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

mié. 8/20

6:25 am-12:28 pm

1 stop6h 03m

Chicago Midway

sáb. 8/23

6:04 am-11:53 am

1 stop5h 49m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 julio 31, 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.

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 julio 31, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and Allegiant Air from Kentucky to Chicago Midway Airport by reading reviews from past customers. 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
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
702 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,239 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $49 on Southwest. Other airlines that offer cheap prices include Allegiant Air from $51 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 Nashville Intl - Chicago Midway, Cincinnati Cinci./N. Kentucky - Chicago Midway or Louisville Intl - 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 $75. While the most popular route (Nashville Intl - Chicago Midway) can be booked for $97 on average our data indicates $292 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
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
Newark to Midway flights
Ontario to O'Hare Intl flights
LaGuardia to Midway flights
Dallas/Fort Worth to Midway flights
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Sky Harbor Intl to O'Hare Intl flights
Atlanta to Midway flights
Dulles Intl to Midway flights
Denver to O'Hare Intl flights
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Burbank to O'Hare Intl flights
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Atlanta to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Baltimore to Midway flights
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Miami to O'Hare Intl flights
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George Bush Intcntl to O'Hare Intl flights
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Minneapolis to O'Hare Intl flights
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Portland to O'Hare Intl flights
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Philadelphia to Midway flights
Hobby to Midway flights
Orlando to O'Hare Intl flights
Minneapolis to Midway flights
Oakland to O'Hare Intl flights
Los Angeles to Midway flights
San Francisco to Midway flights
Tampa to O'Hare Intl flights
Boston to Midway flights
Las Vegas to O'Hare Intl flights
Love Field to Midway flights
Reagan-National 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$275FlexibilityNo cancel feeOn-time63%

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