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Kentucky

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

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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Jul 1 — Jul 81
Tue 7/1
Tue 7/8
1 adult, Economy
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Cheap flight deals from Midway to Kentucky

Keep the following information in mind while searching for Midway to Kentucky flight deals. Data was last updated June 26, 2025.

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

August

Average price

$436

Good round-trip deal

$249 or less

Good one-way deal

$119 or less
From Chicago Midway to Kentucky
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One-way flight from Chicago Midway to Kentucky
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Highest demand for flights based on searches. 16% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Chicago Midway to Kentucky.
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Price to beat on a one-way flight from Chicago Midway to Kentucky.
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Find flight deals from Midway to Kentucky

Cheapest flights from Midway to Kentucky
Explore the most affordable flight options available from Midway to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 26, 2025.

This Southwest deal was found by Cheapflights users on 6/25. 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 8/128:20 pmMDW - BNA
Nonstop1h 30mSouthwest
Wed 8/138:50 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 6/25$97
This Southwest deal was found by Cheapflights users on 6/25. 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 8/73:30 pmMDW - SDF
Nonstop1h 10mSouthwest
Tue 8/121:15 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 6/25$97
This Kiwi.com deal was found by Cheapflights users on 6/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:50 pmMDW - TYS
Nonstop1h 31mAllegiant Air
Mon 9/291:50 pmTYS - MDW
Nonstop1h 36mAllegiant Air
Deal found 6/24$111
This Delta deal was found by Cheapflights users on 6/25. 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 8/1112:43 pmMDW - BNA
1 stop4h 13mDelta
Sun 8/175:15 amBNA - MDW
1 stop4h 21mDelta
Deal found 6/25$177
This Booking.com deal was found by Cheapflights users on 6/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/252:54 pmMDW - TYS
Nonstop1h 26mMultiple Airlines
Sun 7/275:25 pmTYS - MDW
1 stop19h 16mMultiple Airlines
Deal found 6/26$179
This Delta deal was found by Cheapflights users on 6/26. 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.
Tue 8/2610:31 amMDW - SDF
1 stop7h 09mDelta
Sun 8/3110:45 amSDF - MDW
1 stop5h 38mDelta
Deal found 6/26$188
This Mytrip deal was found by Cheapflights users on 6/25. 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 8/88:03 amMDW - CVG
1 stop11h 15mAllegiant Air
Sun 8/105:58 pmCVG - MDW
1 stop14h 15mAllegiant Air
Deal found 6/25$206
This Southwest deal was found by Cheapflights users on 6/25. 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 7/297:45 pmMDW - CVG
Nonstop1h 10mSouthwest
Wed 7/306:30 amCVG - MDW
Nonstop1h 05mSouthwest
Deal found 6/25$209
This Delta deal was found by Cheapflights users on 6/25. 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 7/166:00 amMDW - LEX
1 stop5h 15mDelta
Wed 7/2310:24 amLEX - MDW
1 stop3h 05mDelta
Deal found 6/25$209
This Delta deal was found by Cheapflights users on 6/25. 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.
Sat 8/91:09 pmMDW - TYS
1 stop3h 23mDelta
Sat 8/166:14 pmTYS - MDW
1 stop3h 58mDelta
Deal found 6/25$209
This Frontier deal was found by Cheapflights users on 6/23. 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.
Mon 6/306:20 amMDW - CVG
1 stop7h 00mFrontier
Mon 7/75:10 amCVG - MDW
1 stop10h 56mFrontier
Deal found 6/23$226
This CheapOair deal was found by Cheapflights users on 6/24. 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.
Thu 7/32:44 pmMDW - BNA
1 stop27h 54mFrontier
Sat 7/57:00 amBNA - MDW
1 stop13h 54mFrontier
Deal found 6/24$227

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to Kentucky 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 June 26, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kentucky that are best for you.

Fly from

Midway

Fly to

Kentucky

Route

Depart

Return

Price

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 8/12

8:20 pm-9:50 pm

Nonstop1h 30m

Nashville Intl

Wed 8/13

8:50 pm-10:25 pm

Nonstop1h 35m

$97

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 8/7

3:30 pm-5:40 pm

Nonstop1h 10m

Louisville Intl

Tue 8/12

1:15 pm-1:30 pm

Nonstop1h 15m

$97

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Fri 8/8

2:46 pm-5:12 pm

Nonstop1h 26m

Knoxville McGhee Tyson

Mon 8/25

2:29 pm-3:02 pm

Nonstop1h 33m

$112

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 8/11

12:43 pm-4:56 pm

1 stop4h 13m

Nashville Intl

Sun 8/17

5:15 am-9:36 am

1 stop4h 21m

$177

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Fri 7/25

2:54 pm-5:20 pm

Nonstop1h 26m

Knoxville McGhee Tyson

Sun 7/27

5:25 pm-11:41 am

1 stop19h 16m

$179

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 8/26

10:31 am-6:40 pm

1 stop7h 09m

Louisville Intl

Sun 8/31

10:45 am-3:23 pm

1 stop5h 38m

$188

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Fri 8/8

8:03 am-8:18 pm

1 stop11h 15m

Cincinnati Cinci./N. Kentucky

Sun 8/10

5:58 pm-7:13 am

1 stop14h 15m

$206

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 7/29

7:45 pm-9:55 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Wed 7/30

6:30 am-6:35 am

Nonstop1h 05m

$209

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 7/16

6:00 am-12:15 pm

1 stop5h 15m

Lexington Blue Grass

Wed 7/23

10:24 am-12:29 pm

1 stop3h 05m

$209

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Sat 8/9

1:09 pm-5:32 pm

1 stop3h 23m

Knoxville McGhee Tyson

Sat 8/16

7:50 am-12:28 pm

1 stop5h 38m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

Showing 1-10 of 38 results
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Best time to book a flight from Midway to Kentucky

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kentucky (average of $299). Flying from Chicago Midway Airport to Kentucky in April is currently the most expensive (average of $369). 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 MDW to KY?

Find hourly flight availability from Midway to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 26, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Kentucky as you normally would.

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated June 26, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Allegiant Air from Chicago Midway Airport to Kentucky to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,276 reviews
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.2
Good
712 reviews
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,296 reviews
Southwest
8.0
Very good
4,276 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Food

7.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Midway to Kentucky. 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 Chicago Midway Airport to Kentucky 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 $49 and Delta from $89 one-way.

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

    While some choose either Chicago Midway - Cincinnati Cinci./N. Kentucky or Chicago Midway - Louisville Intl, Chicago Midway - Nashville Intl is the most popular route from Chicago Midway Airport to Kentucky.

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

    Looking at all options, your cheapest flight can be booked for $114. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $97 on average our data indicates $233 when flying from Chicago Midway Airport to Kentucky.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kentucky (average of $299). Flying from Chicago Midway Airport to Kentucky in April is currently the most expensive (average of $369). 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

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Alternative routes for Midway to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Los Angeles flights

Top airline flying from Midway to Kentucky

Discover the top airline that operate flights from Midway to Kentucky. 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 June 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$157Average$545FlexibilityNo cancel feeOn-time63%

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