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$55+ 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$106
(Mytrip)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

August

Average price

$322

Good round-trip deal

$244 or less

Good one-way deal

$83 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. 9% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/26:40 amMDW - BNA
1 stop6h 27mFrontier
Wed 4/166:00 pmBNA - MDW
1 stop6h 21mFrontier
Deal found 2/20$106
This Frontier deal was found by Cheapflights users on 2/19. 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 4/71:10 pmMDW - CVG
1 stop10h 04mFrontier
Thu 4/1012:23 pmCVG - MDW
1 stop6h 08mFrontier
Deal found 2/19$110
This Southwest deal was found by Cheapflights users on 2/19. 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 3/125:40 amMDW - BNA
Nonstop1h 30mSouthwest
Wed 3/199:15 pmBNA - MDW
Nonstop1h 30mSouthwest
Deal found 2/19$117
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/13:35 pmMDW - CVG
1 stop7h 20mSouthwest
Thu 4/36:30 amCVG - MDW
Nonstop1h 10mSouthwest
Deal found 2/20$127
This Southwest deal was found by Cheapflights users on 2/19. 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 5/610:05 amMDW - SDF
Nonstop1h 15mSouthwest
Wed 5/74:10 pmSDF - MDW
1 stop6h 45mSouthwest
Deal found 2/19$127
This Delta deal was found by Cheapflights users on 2/19. 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 4/19:25 amMDW - BNA
1 stop3h 41mDelta
Sat 4/126:10 amBNA - MDW
1 stop6h 22mDelta
Deal found 2/19$177
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/252:55 pmMDW - LEX
1 stop5h 37mDelta
Thu 3/277:30 amLEX - MDW
1 stop6h 06mDelta
Deal found 2/20$177
This Delta deal was found by Cheapflights users on 2/19. 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 5/66:04 amMDW - SDF
1 stop4h 46mDelta
Wed 5/72:15 pmSDF - MDW
1 stop5h 15mDelta
Deal found 2/19$208
This Delta deal was found by Cheapflights users on 2/19. 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 4/112:57 pmMDW - TYS
1 stop5h 33mDelta
Tue 4/157:48 amTYS - MDW
1 stop5h 47mDelta
Deal found 2/19$209
This Frontier deal was found by Cheapflights users on 2/19. 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 3/66:40 amMDW - TYS
1 stop7h 43mFrontier
Sun 3/94:43 pmTYS - MDW
1 stop8h 36mFrontier
Deal found 2/19$210
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/96:00 amMDW - CVG
1 stop4h 55mDelta
Tue 4/156:03 amCVG - MDW
2 stops9h 19mDelta
Deal found 2/20$213
This Mytrip deal was found by Cheapflights users on 2/18. 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 8/152:54 pmMDW - TYS
Nonstop1h 28mAllegiant Air
Sun 8/178:00 amTYS - MDW
1 stop25h 22mAllegiant Air
Deal found 2/18$236

Find flights from Midway to Kentucky within your budget

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 20, 2025.

Fly from

Midway

Fly to

Kentucky

Route

Depart

Return

Price

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 4/2

6:40 am-1:07 pm

1 stop6h 27m

Nashville Intl

Wed 4/16

6:00 pm-12:21 am

1 stop6h 21m

$106

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Mon 4/7

1:10 pm-12:14 am

1 stop10h 04m

Cincinnati Cinci./N. Kentucky

Thu 4/10

12:23 pm-5:31 pm

1 stop6h 08m

$110

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 4/2

8:55 pm-10:25 pm

Nonstop1h 30m

Nashville Intl

Wed 4/9

7:30 pm-9:05 pm

Nonstop1h 35m

$117

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 4/1

3:35 pm-11:55 pm

1 stop7h 20m

Cincinnati Cinci./N. Kentucky

Thu 4/3

6:30 am-6:40 am

Nonstop1h 10m

$127

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 5/6

10:05 am-12:20 pm

Nonstop1h 15m

Louisville Intl

Wed 5/7

4:10 pm-9:55 pm

1 stop6h 45m

$127

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 4/1

9:25 am-1:06 pm

1 stop3h 41m

Nashville Intl

Sat 4/12

6:10 am-12:32 pm

1 stop6h 22m

$177

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 3/25

2:55 pm-9:32 pm

1 stop5h 37m

Lexington Blue Grass

Thu 3/27

7:30 am-12:36 pm

1 stop6h 06m

$177

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 5/6

6:04 am-11:50 am

1 stop4h 46m

Louisville Intl

Wed 5/7

2:15 pm-6:30 pm

1 stop5h 15m

$208

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Fri 4/11

2:57 pm-9:30 pm

1 stop5h 33m

Knoxville McGhee Tyson

Tue 4/15

7:48 am-12:35 pm

1 stop5h 47m

$209

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Thu 3/6

6:40 am-3:23 pm

1 stop7h 43m

Knoxville McGhee Tyson

Sun 3/9

4:43 pm-12:19 am

1 stop8h 36m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 33 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.

Travel insights for flights from Midway to Kentucky

Get recent, data-driven insights about flights from Midway to Kentucky including ideal travel times, pricing trends, and more.

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 20, 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 February 20, 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
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $55 on Frontier. Other airlines that offer cheap prices include Southwest from $59 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 $68. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $117 on average our data indicates $228 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
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