Kentucky

$69+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Apr 24 — May 11
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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 March 25, 2026.

This Southwest deal was found by Cheapflights users on 3/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:40 am
MDW
-
SDF
Nonstop1h 10m
Southwest
Wed 4/227:15 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Deal found 3/24$177
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Mon 5/259:30 pm
MDW
-
TYS
1 stop21h 01m
Allegiant Air
Thu 5/281:22 pm
TYS
-
MDW
Nonstop1h 35m
Allegiant Air
Deal found 3/22$199
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Sun 5/312:47 pm
MDW
-
TYS
Nonstop1h 26m
Multiple Airlines
Mon 6/110:03 pm
TYS
-
MDW
2 stops24h 59m
Multiple Airlines
Deal found 3/22$201
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Mon 5/259:30 pm
MDW
-
TYS
1 stop21h 01m
Allegiant Air
Sun 5/311:22 pm
TYS
-
MDW
Nonstop1h 35m
Allegiant Air
Deal found 3/22$202
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 5/282:47 pm
MDW
-
TYS
Nonstop1h 26m
Multiple Airlines
Mon 6/110:03 pm
TYS
-
MDW
2 stops24h 59m
Multiple Airlines
Deal found 3/22$205
This Southwest deal was found by Cheapflights users on 3/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:45 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Tue 5/197:15 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Deal found 3/24$211
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Thu 5/282:47 pm
MDW
-
TYS
Nonstop1h 26m
Multiple Airlines
Sun 5/316:03 pm
TYS
-
MDW
2 stops28h 59m
Multiple Airlines
Deal found 3/24$211
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/162:15 pm
MDW
-
BNA
2 stops9h 09m
Multiple Airlines
Sat 4/189:30 am
BNA
-
MDW
1 stop6h 30m
Multiple Airlines
Deal found 3/25$212
This Booking.com deal was found by Cheapflights users on 3/20. 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.
Sun 7/262:48 pm
MDW
-
TYS
Nonstop1h 30m
Allegiant Air
Sun 8/21:22 pm
TYS
-
MDW
Nonstop1h 36m
Allegiant Air
Deal found 3/20$212
This Southwest deal was found by Cheapflights users on 3/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:35 pm
MDW
-
BNA
Nonstop1h 25m
Southwest
Tue 4/2811:55 am
BNA
-
MDW
Nonstop1h 35m
Southwest
Deal found 3/23$213
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 5/282:47 pm
MDW
-
TYS
Nonstop1h 26m
Multiple Airlines
Fri 5/2910:03 pm
TYS
-
MDW
2 stops24h 59m
Multiple Airlines
Deal found 3/22$213
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:14 am
MDW
-
BNA
1 stop7h 44m
Multiple Airlines
Tue 4/219:30 am
BNA
-
MDW
2 stops12h 44m
Multiple Airlines
Deal found 3/25$214

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 March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Southwest)

One-way from

$69
(Kiwi.com)

Popular in

June

Cheapest in

August

Average price

$452

Good round-trip deal

$297 or less

Good one-way deal

$127 or less
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
From Chicago Midway to Kentucky
One-way flight from Chicago Midway to Kentucky
Highest demand for flights based on searches. 9% potential increase in price ($32 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in March 2026
Price to beat on a round-trip flight from Chicago Midway to Kentucky.
Price to beat on a one-way flight from Chicago Midway to Kentucky.

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 25, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kentucky that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 4/21

9:50 am-11:15 am

Nonstop1h 25m

Nashville Intl

Tue 4/28

11:30 am-4:55 pm

2 stops5h 25m

$228

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 4/23

7:45 am-9:55 am

Nonstop1h 10m

Louisville Intl

Mon 4/27

8:10 pm-8:25 pm

Nonstop1h 15m

$244

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

$249

ChicagoBlountville

MDW - TRI

MDWTRI

Chicago Midway

Wed 5/27

10:59 am-7:01 pm

1 stop7h 02m

Blountville Tri Cities TN/VA

Sat 5/30

4:49 pm-9:09 pm

1 stop5h 20m

$249

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 5/2

11:18 am-4:50 pm

1 stop5h 32m

Nashville Intl

Tue 5/5

11:19 am-4:26 pm

1 stop5h 07m

$256

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 6/4

7:15 am-8:40 am

Nonstop1h 25m

Nashville Intl

Mon 6/8

8:25 pm-9:55 pm

Nonstop1h 30m

$261

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Wed 5/6

5:21 pm-11:54 pm

1 stop5h 33m

Lexington Blue Grass

Sat 5/16

3:32 pm-9:09 pm

1 stop6h 37m

$269

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Sat 6/6

5:30 pm-12:01 am

1 stop5h 31m

Knoxville McGhee Tyson

Fri 6/12

7:30 am-12:30 pm

1 stop6h 00m

$269

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Wed 5/6

12:50 pm-3:00 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Wed 5/13

7:35 pm-7:50 pm

Nonstop1h 15m

$271

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 4/21

8:35 pm-10:00 pm

Nonstop1h 25m

Nashville Intl

Sat 4/25

5:15 am-6:50 am

Nonstop1h 35m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/23

Showing 1-10 of 60 resultsSorted by cheapest first
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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 25, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 27% 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 March 23, 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 March 25, 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.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 25m. Fly via Southwest or Delta to get the fastest option. Chicago Midway Airport and Kentucky are separated by a distance of 395 mi. This flight may include one or multiple stops.

  • What are the most popular routes 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 $123. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $205 on average, our data indicates $316 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.

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 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$124Average$255FlexibilityNo cancel feeOn-time63%

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