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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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

August

Average price

$343

Good round-trip deal

$225 or less

Good one-way deal

$137 or less
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
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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. 17% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($18 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 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 April 17, 2025.

This Southwest deal was found by Cheapflights users on 4/16. 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 5/125:20 amMDW - BNA
Nonstop1h 25mSouthwest
Mon 5/199:25 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 4/16$97
This Frontier deal was found by Cheapflights users on 4/16. 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 5/151:19 pmMDW - CVG
1 stop10h 40mFrontier
Fri 5/165:45 amCVG - MDW
1 stop7h 39mFrontier
Deal found 4/16$160
This CheapOair deal was found by Cheapflights users on 4/16. 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 5/81:19 pmMDW - BNA
1 stop19h 50mFrontier
Sun 5/117:52 pmBNA - MDW
1 stop23h 16mFrontier
Deal found 4/16$161
This Southwest deal was found by Cheapflights users on 4/16. 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 6/256:55 amMDW - SDF
1 stop5h 25mSouthwest
Sat 6/286:00 pmSDF - MDW
Nonstop1h 20mSouthwest
Deal found 4/16$171
This Delta deal was found by Cheapflights users on 4/16. 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 5/81:08 pmMDW - SDF
1 stop4h 21mDelta
Mon 5/122:38 pmSDF - MDW
1 stop5h 07mDelta
Deal found 4/16$177
This Delta deal was found by Cheapflights users on 4/16. 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 5/176:00 amMDW - BNA
1 stop6h 18mDelta
Wed 5/215:15 amBNA - MDW
1 stop6h 38mDelta
Deal found 4/16$178
This Mytrip deal was found by Cheapflights users on 4/15. 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 5/232:54 pmMDW - TYS
Nonstop1h 28mAllegiant Air
Sun 5/258:00 amTYS - MDW
1 stop25h 22mAllegiant Air
Deal found 4/15$193
This Delta deal was found by Cheapflights users on 4/16. 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 5/216:00 amMDW - TYS
1 stop4h 23mDelta
Sun 5/255:45 amTYS - MDW
1 stop4h 55mDelta
Deal found 4/16$204
This Delta deal was found by Cheapflights users on 4/16. 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 5/134:15 pmMDW - LEX
1 stop4h 20mDelta
Tue 5/203:44 pmLEX - MDW
1 stop6h 43mDelta
Deal found 4/16$209
This Southwest deal was found by Cheapflights users on 4/16. 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 5/104:50 pmMDW - CVG
1 stop5h 35mSouthwest
Sun 5/116:50 amCVG - MDW
Nonstop1h 10mSouthwest
Deal found 4/16$221
This Delta deal was found by Cheapflights users on 4/17. 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 5/106:00 amMDW - CVG
1 stop4h 06mDelta
Sun 5/116:00 amCVG - MDW
1 stop4h 40mDelta
Deal found 4/17$231
This Delta deal was found by Cheapflights users on 4/16. 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 5/3010:25 amMDW - TRI
1 stop3h 44mDelta
Sun 6/16:10 amTRI - MDW
1 stop4h 30mDelta
Deal found 4/16$239

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 April 17, 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

Mon 5/12

5:20 am-6:45 am

Nonstop1h 25m

Nashville Intl

Mon 5/19

9:25 pm-11:00 pm

Nonstop1h 35m

$97

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 5/15

1:19 pm-12:59 am

1 stop10h 40m

Cincinnati Cinci./N. Kentucky

Fri 5/16

5:45 am-12:24 pm

1 stop7h 39m

$160

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 5/8

1:19 pm-9:09 am

1 stop19h 50m

Nashville Intl

Sun 5/11

7:52 pm-7:08 pm

1 stop23h 16m

$161

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 6/25

6:55 am-1:20 pm

1 stop5h 25m

Louisville Intl

Sat 6/28

6:00 pm-6:20 pm

Nonstop1h 20m

$171

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 5/8

1:08 pm-6:29 pm

1 stop4h 21m

Louisville Intl

Mon 5/12

2:38 pm-6:45 pm

1 stop5h 07m

$177

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 5/17

6:00 am-12:18 pm

1 stop6h 18m

Nashville Intl

Wed 5/21

5:15 am-11:53 am

1 stop6h 38m

$178

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Fri 5/23

2:54 pm-5:22 pm

Nonstop1h 28m

Knoxville McGhee Tyson

Sun 5/25

8:00 am-8:22 am

1 stop25h 22m

$193

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Wed 5/21

6:00 am-11:23 am

1 stop4h 23m

Knoxville McGhee Tyson

Sun 5/25

5:45 am-9:40 am

1 stop4h 55m

$204

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 5/13

4:15 pm-9:35 pm

1 stop4h 20m

Lexington Blue Grass

Tue 5/20

3:44 pm-9:27 pm

1 stop6h 43m

$209

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Sat 5/10

4:50 pm-11:25 pm

1 stop5h 35m

Cincinnati Cinci./N. Kentucky

Sun 5/11

6:50 am-7:00 am

Nonstop1h 10m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 37 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 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 April 17, 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.

Rainfall in Kentucky by month

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

In terms of precipitation, rainfall in Kentucky ranges from 3.1 - 5.3 inches per month. May is typically the wettest month, when rainfall can reach 5.3 in. September is typically the driest time to visit Kentucky when rainfall is around 3.1 in.

Temperature in Kentucky by month

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

If weather is an important factor for your trip to Kentucky, 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 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 35.6 F).

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 April 17, 2025.
Read through reviews of airlines operating flights from Chicago to Kentucky, such as Southwest, Delta and Allegiant Air. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,281 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Frontier from $80 and Allegiant Air from $89 one-way.

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

    While some choose either Chicago Midway - Knoxville McGhee Tyson or Chicago Midway - Cincinnati Cinci./N. Kentucky, 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 $82. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $97 on average our data indicates $257 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.

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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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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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$157Average$539FlexibilityNo cancel feeOn-time63%

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