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$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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
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 November 20, 2024.

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 November 20, 2024.

This Southwest deal was found by Cheapflights users on 11/20. 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.
Wed 12/117:30 pmMDW - BNA
Nonstop1h 30mSouthwest
Sun 12/156:55 amBNA - MDW
Nonstop1h 35mSouthwest
Deal found 11/20$98
This Southwest deal was found by Cheapflights users on 11/19. 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 12/177:30 pmMDW - SDF
Nonstop1h 10mSouthwest
Tue 12/241:55 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 11/19$138
This Cheapflightsfares deal was found by Cheapflights users on 11/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/223:14 pmMDW - TYS
Nonstop1h 27mAllegiant Air
Mon 11/251:50 pmTYS - MDW
Nonstop1h 34mAllegiant Air
Deal found 11/19$153
This Delta deal was found by Cheapflights users on 11/20. 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 12/116:00 amMDW - BNA
1 stop5h 44mDelta
Mon 12/166:25 amBNA - MDW
1 stop6h 25mDelta
Deal found 11/20$176
This Delta deal was found by Cheapflights users on 11/19. 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 12/105:50 pmMDW - SDF
1 stop4h 09mDelta
Wed 12/111:50 pmSDF - MDW
1 stop5h 42mDelta
Deal found 11/19$176
This Delta deal was found by Cheapflights users on 11/20. 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.
Sat 12/1410:38 amMDW - TYS
1 stop3h 20mDelta
Mon 12/166:38 pmTYS - MDW
1 stop4h 28mDelta
Deal found 11/20$188
This Delta deal was found by Cheapflights users on 11/18. 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.
Tue 12/106:00 amMDW - LEX
1 stop5h 29mDelta
Tue 12/105:56 pmLEX - MDW
1 stop5h 10mDelta
Deal found 11/18$196
This Frontier deal was found by Cheapflights users on 11/19. 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 12/236:00 amMDW - CVG
1 stop10h 35mFrontier
Wed 12/255:05 amCVG - MDW
1 stop9h 15mFrontier
Deal found 11/19$198
This Frontier deal was found by Cheapflights users on 11/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/127:15 amMDW - TYS
1 stop7h 01mFrontier
Sun 12/154:19 pmTYS - MDW
1 stop8h 54mFrontier
Deal found 11/20$208
This Southwest deal was found by Cheapflights users on 11/19. 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 12/189:00 amMDW - CVG
1 stop5h 25mSouthwest
Thu 12/196:50 amCVG - MDW
Nonstop1h 15mSouthwest
Deal found 11/19$212
This Delta deal was found by Cheapflights users on 11/19. 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.
Wed 12/189:30 amMDW - CVG
2 stops8h 23mDelta
Thu 12/196:00 amCVG - MDW
1 stop3h 50mDelta
Deal found 11/19$237
This Delta deal was found by Cheapflights users on 11/20. 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 12/186:00 amMDW - TRI
1 stop5h 15mDelta
Wed 12/256:00 amTRI - MDW
1 stop4h 23mDelta
Deal found 11/20$243

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 12/11

7:30 pm-9:00 pm

Nonstop1h 30m

Nashville Intl

Sat 12/14

4:15 pm-5:50 pm

Nonstop1h 35m

$98

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 1/24

7:15 am-1:44 pm

1 stop6h 29m

Nashville Intl

Sun 1/26

5:43 pm-12:17 am

1 stop6h 34m

$126

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 12/17

7:30 pm-9:40 pm

Nonstop1h 10m

Louisville Intl

Tue 12/24

1:55 pm-2:10 pm

Nonstop1h 15m

$138

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 12/11

6:00 am-11:44 am

1 stop5h 44m

Nashville Intl

Mon 12/16

6:25 am-12:50 pm

1 stop6h 25m

$176

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 12/10

5:50 pm-10:59 pm

1 stop4h 09m

Louisville Intl

Wed 12/11

1:50 pm-6:32 pm

1 stop5h 42m

$176

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Sat 12/14

10:38 am-2:58 pm

1 stop3h 20m

Knoxville McGhee Tyson

Mon 12/16

6:38 pm-10:06 pm

1 stop4h 28m

$188

ChicagoLexington

MDW - LEX

MDWLEX

Chicago Midway

Tue 1/14

6:00 am-12:31 pm

1 stop5h 31m

Lexington Blue Grass

Wed 1/15

7:40 am-1:08 pm

1 stop6h 28m

$196

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Mon 12/23

6:00 am-5:35 pm

1 stop10h 35m

Cincinnati Cinci./N. Kentucky

Wed 12/25

5:05 am-1:20 pm

1 stop9h 15m

$198

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Wed 12/18

9:00 am-3:25 pm

1 stop5h 25m

Cincinnati Cinci./N. Kentucky

Thu 12/19

6:50 am-7:05 am

Nonstop1h 15m

$212

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Wed 1/15

9:34 am-1:49 pm

1 stop3h 15m

Cincinnati Cinci./N. Kentucky

Thu 1/16

6:30 am-12:46 pm

1 stop7h 16m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 46 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 November 20, 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 November 20, 2024.
Read through reviews of airlines operating flights from Chicago to Kentucky, such as Frontier, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Allegiant Air
7.4
Good
850 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Allegiant Air from $86 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 - Louisville Intl, 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 $86. While the most popular route (Chicago Midway - Nashville Intl) can be booked for $98 on average our data indicates $389 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 $298). Flying from Chicago Midway Airport to Kentucky in April is currently the most expensive (average of $370). 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
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