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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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$137
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

August

Average price

$395

Good round-trip deal

$250 or less

Good one-way deal

$180 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. 21% potential increase in price ($84 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 March 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 March 28, 2025.

This Southwest deal was found by Cheapflights users on 3/27. 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 5/129:25 amMDW - BNA
Nonstop1h 30mSouthwest
Tue 5/135:15 pmBNA - MDW
Nonstop1h 40mSouthwest
Deal found 3/27$137
This Frontier deal was found by Cheapflights users on 3/27. 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.
Tue 4/86:00 amMDW - CVG
1 stop6h 52mFrontier
Tue 4/84:31 pmCVG - MDW
1 stop8h 50mFrontier
Deal found 3/27$155
This Frontier deal was found by Cheapflights users on 3/27. 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 4/186:45 amMDW - BNA
1 stop6h 24mFrontier
Mon 4/216:00 pmBNA - MDW
1 stop6h 21mFrontier
Deal found 3/27$158
This Southwest deal was found by Cheapflights users on 3/25. 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.
Fri 5/308:55 pmMDW - SDF
Nonstop1h 15mSouthwest
Mon 6/26:15 pmSDF - MDW
1 stop4h 45mSouthwest
Deal found 3/25$166
This Delta deal was found by Cheapflights users on 3/27. 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 4/176:04 amMDW - BNA
1 stop5h 20mDelta
Mon 4/215:15 amBNA - MDW
1 stop3h 52mDelta
Deal found 3/27$177
This Delta deal was found by Cheapflights users on 3/26. 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.
Sat 5/101:08 pmMDW - SDF
1 stop4h 21mDelta
Sat 5/177:05 amSDF - MDW
2 stops6h 23mDelta
Deal found 3/26$182
This Frontier deal was found by Cheapflights users on 3/27. 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 4/106:45 amMDW - TYS
1 stop7h 56mFrontier
Thu 4/174:31 pmTYS - MDW
1 stop8h 50mFrontier
Deal found 3/27$188
This Delta deal was found by Cheapflights users on 3/27. 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 5/136:00 amMDW - TYS
1 stop6h 19mDelta
Tue 5/207:47 amTYS - MDW
1 stop5h 41mDelta
Deal found 3/27$199
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Sat 5/242:44 pmMDW - TYS
1 stop24h 51mMultiple Airlines
Mon 5/261:31 pmTYS - MDW
Nonstop1h 33mMultiple Airlines
Deal found 3/27$207
This Southwest deal was found by Cheapflights users on 3/27. 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 6/36:25 pmMDW - CVG
Nonstop1h 10mSouthwest
Thu 6/56:35 amCVG - MDW
Nonstop1h 10mSouthwest
Deal found 3/27$229
This Delta deal was found by Cheapflights users on 3/27. 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 4/293:02 pmMDW - LEX
1 stop5h 32mDelta
Sat 5/36:00 amLEX - MDW
1 stop4h 07mDelta
Deal found 3/27$235
This Mytrip deal was found by Cheapflights users on 3/27. 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 6/138:36 pmMDW - TYS
2 stops25h 02mAllegiant Air
Mon 6/161:29 pmTYS - MDW
Nonstop1h 34mAllegiant Air
Deal found 3/27$241

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 March 28, 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

9:25 am-10:55 am

Nonstop1h 30m

Nashville Intl

Tue 5/13

5:15 pm-6:55 pm

Nonstop1h 40m

$137

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 4/8

6:00 am-1:52 pm

1 stop6h 52m

Cincinnati Cinci./N. Kentucky

Tue 4/8

4:31 pm-12:21 am

1 stop8h 50m

$155

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 4/18

6:45 am-1:09 pm

1 stop6h 24m

Nashville Intl

Mon 4/21

6:00 pm-12:21 am

1 stop6h 21m

$158

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Fri 5/30

8:55 pm-11:10 pm

Nonstop1h 15m

Louisville Intl

Mon 6/2

6:15 pm-10:00 pm

1 stop4h 45m

$166

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 4/17

6:04 am-11:24 am

1 stop5h 20m

Nashville Intl

Mon 4/21

5:15 am-9:07 am

1 stop3h 52m

$177

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Sat 5/10

1:08 pm-6:29 pm

1 stop4h 21m

Louisville Intl

Sat 5/17

7:05 am-12:28 pm

2 stops6h 23m

$182

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Thu 4/10

6:45 am-3:41 pm

1 stop7h 56m

Knoxville McGhee Tyson

Thu 4/17

4:31 pm-12:21 am

1 stop8h 50m

$188

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Tue 5/13

6:00 am-1:19 pm

1 stop6h 19m

Knoxville McGhee Tyson

Tue 5/20

7:47 am-12:28 pm

1 stop5h 41m

$199

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Sat 5/24

2:44 pm-4:35 pm

1 stop24h 51m

Knoxville McGhee Tyson

Mon 5/26

1:31 pm-2:04 pm

Nonstop1h 33m

$207

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 6/3

6:25 pm-8:35 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Thu 6/5

6:35 am-6:45 am

Nonstop1h 10m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 34 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 March 28, 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 March 28, 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
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

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
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

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
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

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
731 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

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
3,271 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

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 $79 and Delta 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 $137 on average our data indicates $330 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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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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$157Average$539FlexibilityNo cancel feeOn-time63%
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