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Kentucky

$56+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 2/266:25 am
MDW
-
CVG
1 stop10h 07m
Frontier
Sun 3/16:42 pm
CVG
-
MDW
1 stop20h 47m
Frontier
Deal found 2/10$147
This deal was found by Cheapflights users on 2/8. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
MDW
-
TRI
1 stop6h 03m
Delta
Fri 4/247:15 pm
TRI
-
MDW
1 stop4h 13m
Delta
Deal found 2/8$159
This Frontier deal was found by Cheapflights users on 2/11. 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 2/267:30 am
MDW
-
CVG
1 stop9h 39m
Frontier
Mon 3/21:07 pm
CVG
-
MDW
1 stop10h 22m
Frontier
Deal found 2/11$160
This Southwest deal was found by Cheapflights users on 2/10. 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 3/186:05 pm
MDW
-
CVG
Nonstop1h 10m
Southwest
Wed 3/257:35 pm
CVG
-
MDW
Nonstop1h 10m
Southwest
Deal found 2/10$164
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Thu 3/57:30 am
MDW
-
CVG
1 stop9h 02m
Frontier
Mon 3/911:58 am
CVG
-
MDW
1 stop12h 22m
Frontier
Deal found 2/10$166
This Delta deal was found by Cheapflights users on 2/10. 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 3/46:00 am
MDW
-
TRI
1 stop5h 17m
Delta
Mon 3/97:17 pm
TRI
-
MDW
1 stop4h 14m
Delta
Deal found 2/10$169
This Southwest deal was found by Cheapflights users on 2/9. 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 4/76:10 pm
MDW
-
CVG
Nonstop1h 10m
Southwest
Sat 4/115:00 pm
CVG
-
MDW
Nonstop1h 15m
Southwest
Deal found 2/9$171
This Southwest deal was found by Cheapflights users on 2/11. 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 3/119:20 am
MDW
-
CVG
1 stop7h 20m
Southwest
Wed 3/186:15 pm
CVG
-
MDW
1 stop5h 35m
Southwest
Deal found 2/11$177
This Southwest deal was found by Cheapflights users on 2/10. 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 3/106:15 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Tue 3/177:05 pm
SDF
-
MDW
Nonstop1h 20m
Southwest
Deal found 2/10$177
This Southwest deal was found by Cheapflights users on 2/9. 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 5/137:50 am
MDW
-
CVG
2 stops8h 15m
Southwest
Mon 5/188:20 pm
CVG
-
MDW
Nonstop1h 10m
Southwest
Deal found 2/9$179
This Frontier deal was found by Cheapflights users on 2/9. 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 2/196:15 am
MDW
-
CVG
1 stop9h 22m
Frontier
Mon 2/231:07 pm
CVG
-
MDW
1 stop7h 40m
Frontier
Deal found 2/9$181
This Delta deal was found by Cheapflights users on 2/11. 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 3/111:10 pm
MDW
-
CVG
2 stops9h 49m
Delta
Wed 3/188:15 am
CVG
-
MDW
1 stop5h 14m
Delta
Deal found 2/11$182

Find flight deals from Midway to Kentucky

Keep the following information in mind while searching for Midway to Kentucky flight deals. Data was last updated February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$147
(Kiwi.com)

One-way from

$56
(Southwest)

Popular in

June

Cheapest in

August

Average price

$376

Good round-trip deal

$329 or less

Good one-way deal

$127 or less
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
Search Deals
From Chicago Midway to Kentucky
Search Deals
One-way flight from Chicago Midway to Kentucky
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Kentucky.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Kentucky.
Search Deals

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 February 12, 2026.
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

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/26

6:25 am-5:32 pm

1 stop10h 07m

Cincinnati Cinci./N. Kentucky

Sun 3/1

6:42 pm-2:29 pm

1 stop20h 47m

$147

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Tue 4/21

6:00 am-1:03 pm

1 stop6h 03m

Blountville Tri Cities TN/VA

Tue 4/28

7:15 pm-10:28 pm

1 stop4h 13m

$159

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Tue 4/21

6:00 am-1:03 pm

1 stop6h 03m

Blountville Tri Cities TN/VA

Fri 4/24

7:15 pm-10:28 pm

1 stop4h 13m

$159

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Wed 4/22

6:00 am-1:03 pm

1 stop6h 03m

Blountville Tri Cities TN/VA

Sat 4/25

5:08 pm-10:28 pm

1 stop6h 20m

$159

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Wed 4/22

6:00 am-1:03 pm

1 stop6h 03m

Blountville Tri Cities TN/VA

Tue 4/28

7:15 pm-10:28 pm

1 stop4h 13m

$159

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Wed 3/4

6:00 am-12:17 pm

1 stop5h 17m

Blountville Tri Cities TN/VA

Mon 3/9

7:17 pm-10:31 pm

1 stop4h 14m

$159

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 4/7

6:10 pm-8:20 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Sat 4/11

5:00 pm-5:15 pm

Nonstop1h 15m

$171

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Wed 5/13

8:00 am-12:40 pm

1 stop3h 40m

Cincinnati Cinci./N. Kentucky

Mon 5/18

8:20 pm-8:30 pm

Nonstop1h 10m

$174

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Wed 3/11

9:20 am-5:40 pm

1 stop7h 20m

Cincinnati Cinci./N. Kentucky

Wed 3/18

6:15 pm-10:50 pm

1 stop5h 35m

$177

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 4/16

6:00 am-6:36 pm

1 stop11h 36m

Cincinnati Cinci./N. Kentucky

Mon 4/20

1:05 pm-10:21 pm

1 stop10h 16m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 60 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 February 12, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 25% on flights from Chicago Midway Airport to Kentucky by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Chicago Midway Airport to Kentucky?

Use this chart to determine the cheapest time to fly round-trip from Midway to Kentucky. Price data was last updated on February 7, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Kentucky flight should consider departing on Monday evenings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 February 12, 2026.
Peruse reviews from past customers who have flown with Southwest 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
4,280 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago Midway Airport to Kentucky?

    There are many flights that can get you from Chicago Midway Airport to Kentucky in 1h 10m. Fly via Frontier, Delta, or Southwest to get the fastest option. Chicago Midway Airport and Kentucky are separated by a distance of 249 mi. This flight may include one or multiple stops.

  • 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 $118. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $191 on average, our data indicates $314 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.

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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O'Hare Intl to Reagan-National flights
O'Hare Intl to Dulles Intl flights
Midway to LaGuardia flights
Midway to Tampa flights
O'Hare Intl to Charleston flights
O'Hare Intl to Salt Lake City flights
Midway to Atlanta flights
O'Hare Intl to Savannah flights
O'Hare Intl to Sarasota flights
Midway to Fort Myers flights
Midway to Newark 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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$124Average$360FlexibilityNo cancel feeOn-time63%

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