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$54+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Midway to Kentucky

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kentucky (USKY). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$129
(Southwest)

One-way from

$54
(Mytrip)
From Chicago Midway to Kentucky
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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 December 18, 2024.

This Delta deal was found by Cheapflights users on 12/17. 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.
Wed 12/259:30 amMDW - BNA
1 stop4h 09mDelta
Wed 1/227:15 amBNA - MDW
1 stop4h 44mDelta
Deal found 12/17$221
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/255:30 pmMDW - BNA
Nonstop1h 30mSouthwest
Wed 1/17:30 amBNA - MDW
Nonstop1h 35mSouthwest
Deal found 12/17$248
This Delta deal was found by Cheapflights users on 12/17. 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.
Tue 12/245:51 pmMDW - CVG
1 stop4h 03mDelta
Wed 1/16:00 amCVG - MDW
1 stop3h 50mDelta
Deal found 12/17$258
This CheapOair deal was found by Cheapflights users on 12/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/202:35 pmMDW - CVG
1 stop8h 14mFrontier
Sun 12/226:57 pmCVG - MDW
1 stop18h 32mFrontier
Deal found 12/17$338
This Delta deal was found by Cheapflights users on 12/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/186:00 amMDW - TYS
1 stop3h 57mDelta
Sun 12/226:10 amTYS - MDW
1 stop5h 58mDelta
Deal found 12/18$368
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/298:35 pmMDW - CVG
Nonstop1h 10mSouthwest
Sat 1/185:05 pmCVG - MDW
Nonstop1h 10mSouthwest
Deal found 12/17$392
This Southwest deal was found by Cheapflights users on 12/16. 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 12/2510:00 amMDW - SDF
Nonstop1h 15mSouthwest
Thu 12/266:40 amSDF - MDW
Nonstop1h 20mSouthwest
Deal found 12/16$405
This Delta deal was found by Cheapflights users on 12/17. 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.
Sun 12/296:25 pmMDW - LEX
1 stop3h 35mDelta
Sat 1/1812:04 pmLEX - MDW
1 stop5h 08mDelta
Deal found 12/17$407
This Mytrip deal was found by Cheapflights users on 12/18. 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.
Sun 12/227:14 pmMDW - BNA
2 stops24h 54mMultiple Airlines
Mon 1/66:54 pmBNA - MDW
1 stop13h 55mMultiple Airlines
Deal found 12/18$463
This Delta deal was found by Cheapflights users on 12/17. 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.
Tue 12/245:51 pmMDW - SDF
1 stop3h 36mDelta
Sat 12/2812:29 pmSDF - MDW
1 stop4h 55mDelta
Deal found 12/17$473
This CheapOair deal was found by Cheapflights users on 12/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/287:00 amMDW - BNA
1 stop13h 06mFrontier
Fri 1/35:07 pmBNA - MDW
1 stop20h 01mFrontier
Deal found 12/17$589
This Gotogate deal was found by Cheapflights users on 12/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2510:27 pmMDW - TYS
1 stop19h 26mFrontier
Sun 12/297:43 pmTYS - MDW
1 stop26h 26mFrontier
Deal found 12/17$707

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 2/15

5:50 pm-7:20 pm

Nonstop1h 30m

Nashville Intl

Wed 2/19

2:30 pm-4:05 pm

Nonstop1h 35m

$129

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 1/14

10:05 am-12:20 pm

Nonstop1h 15m

Louisville Intl

Thu 1/16

7:15 pm-7:30 pm

Nonstop1h 15m

$153

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 1/31

2:08 pm-8:56 pm

1 stop6h 48m

Nashville Intl

Fri 2/7

2:20 pm-6:11 pm

1 stop3h 51m

$176

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 1/14

10:57 am-3:56 pm

1 stop3h 59m

Louisville Intl

Tue 1/21

7:05 am-10:12 am

1 stop4h 07m

$176

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Wed 1/22

10:57 am-6:37 pm

1 stop6h 40m

Knoxville McGhee Tyson

Sat 1/25

12:08 pm-2:53 pm

1 stop3h 45m

$188

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 2/28

6:40 am-1:23 pm

1 stop6h 43m

Nashville Intl

Mon 3/3

6:01 pm-12:17 am

1 stop6h 16m

$206

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 1/9

6:30 pm-8:45 pm

Nonstop1h 15m

Cincinnati Cinci./N. Kentucky

Mon 1/13

7:15 am-7:20 am

Nonstop1h 05m

$210

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Fri 2/7

6:40 am-4:48 pm

1 stop9h 08m

Cincinnati Cinci./N. Kentucky

Fri 2/14

7:51 pm-12:17 am

2 stops29h 26m

$211

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 1/28

2:08 pm-9:41 pm

1 stop6h 33m

Lexington Blue Grass

Sat 2/1

12:04 pm-4:12 pm

1 stop5h 08m

$211

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Sun 1/19

7:15 am-3:19 pm

1 stop7h 04m

Knoxville McGhee Tyson

Thu 1/23

4:19 pm-12:17 am

1 stop8h 58m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 30 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 December 18, 2024.

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 December 18, 2024.
Read through reviews of airlines operating flights from Chicago to Kentucky, such as Southwest, Frontier and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Entertainment

7.7

Overall

8.1

Comfort

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $54 on Frontier. Other airlines that offer cheap prices include Southwest from $59 and Delta from $88 one-way.

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

    While some choose either Chicago Midway - Nashville Intl or Chicago Midway - Knoxville McGhee Tyson, Chicago Midway - Cincinnati Cinci./N. Kentucky 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 $284. While the most popular route (Chicago Midway - Cincinnati Cinci./N. Kentucky) can be booked for $186 on average our data indicates $315 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
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