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$54+ Cheap flights from Kentucky to Midway (MDW)

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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Kentucky to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Kentucky (USKY) to Midway (MDW). 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 21, 2024.

Find flight deals from Kentucky to Midway

Cheapest flights from Kentucky to Midway
Explore the most affordable flight options available from Kentucky to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 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.
Fri 12/137:35 pmBNA - MDW
Nonstop1h 35mSouthwest
Sat 12/146:00 amMDW - BNA
Nonstop1h 30mSouthwest
Deal found 11/20$98
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/67:13 pmBNA - MDW
1 stop5h 07mFrontier
Sun 12/87:15 amMDW - BNA
1 stop6h 39mFrontier
Deal found 11/20$125
This Cheapflightsfares deal was found by Cheapflights users on 11/21. 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.
Mon 11/251:50 pmTYS - MDW
Nonstop1h 34mAllegiant Air
Wed 11/276:16 pmMDW - TYS
Nonstop1h 27mAllegiant Air
Deal found 11/21$166
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.
Mon 12/166:25 amBNA - MDW
1 stop6h 25mDelta
Thu 12/196:00 amMDW - BNA
1 stop3h 55mDelta
Deal found 11/20$176
This Delta deal was found by Cheapflights users on 11/21. 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 12/1710:10 amCVG - MDW
1 stop3h 40mDelta
Tue 12/245:51 pmMDW - CVG
1 stop4h 03mDelta
Deal found 11/21$176
This Southwest deal was found by Cheapflights users on 11/21. 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.
Thu 12/127:25 amCVG - MDW
Nonstop1h 15mSouthwest
Sun 12/158:25 pmMDW - CVG
Nonstop1h 10mSouthwest
Deal found 11/21$178
This Delta deal was found by Cheapflights users on 11/21. 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.
Mon 12/1612:23 pmTYS - MDW
1 stop5h 38mDelta
Tue 12/1712:44 pmMDW - TYS
1 stop5h 09mDelta
Deal found 11/21$188
This Southwest deal was found by Cheapflights users on 11/21. 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.
Fri 12/136:05 pmSDF - MDW
Nonstop1h 15mSouthwest
Sun 12/153:10 pmMDW - SDF
Nonstop1h 10mSouthwest
Deal found 11/21$208
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.
Fri 12/205:01 amCVG - MDW
1 stop8h 28mFrontier
Wed 12/252:20 pmMDW - CVG
1 stop8h 36mFrontier
Deal found 11/20$208
This Delta deal was found by Cheapflights users on 11/21. 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.
Thu 12/122:29 pmSDF - MDW
1 stop3h 32mDelta
Sun 12/156:00 amMDW - SDF
1 stop4h 44mDelta
Deal found 11/21$212
This Delta deal was found by Cheapflights users on 11/21. 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 12/1111:28 amLEX - MDW
1 stop6h 33mDelta
Wed 12/186:00 amMDW - LEX
1 stop5h 29mDelta
Deal found 11/21$237
This Booking.com deal was found by Cheapflights users on 11/21. 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.
Mon 11/257:08 pmTYS - MDW
1 stop19h 02mMultiple Airlines
Wed 11/276:16 pmMDW - TYS
Nonstop1h 27mMultiple Airlines
Deal found 11/21$265

Find flights from Kentucky to Midway within your budget

Customize your flight search to find flights from Kentucky to Midway 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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 1/11

10:10 am-11:45 am

Nonstop1h 35m

Chicago Midway

Sat 1/11

2:05 pm-3:35 pm

Nonstop1h 30m

$93

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 12/6

7:13 pm-12:20 am

1 stop5h 07m

Chicago Midway

Sun 12/8

7:15 am-1:54 pm

1 stop6h 39m

$125

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 1/9

6:50 am-12:46 pm

1 stop6h 56m

Chicago Midway

Mon 1/13

6:00 am-11:39 am

1 stop4h 39m

$176

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 1/8

6:15 am-1:08 pm

1 stop6h 53m

Chicago Midway

Mon 1/13

6:00 am-12:58 pm

1 stop6h 58m

$176

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 12/17

10:10 am-12:50 pm

1 stop3h 40m

Chicago Midway

Tue 12/24

5:51 pm-10:54 pm

1 stop4h 03m

$176

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sun 2/16

7:00 am-7:15 am

Nonstop1h 15m

Chicago Midway

Mon 2/24

7:35 pm-9:50 pm

Nonstop1h 15m

$178

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 12/12

7:25 am-7:40 am

Nonstop1h 15m

Chicago Midway

Sun 12/15

8:25 pm-10:35 pm

Nonstop1h 10m

$178

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 1/9

6:36 am-12:46 pm

1 stop7h 10m

Chicago Midway

Sat 1/11

5:05 pm-10:26 pm

1 stop4h 21m

$188

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Sat 1/18

5:56 pm-10:20 pm

1 stop5h 24m

Chicago Midway

Tue 1/21

2:08 pm-9:41 pm

1 stop6h 33m

$202

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Fri 12/20

5:01 am-12:29 pm

1 stop8h 28m

Chicago Midway

Wed 12/25

2:20 pm-11:56 pm

1 stop8h 36m

$208

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 42 results
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Best time to book a flight from Kentucky to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Kentucky 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 Kentucky to Midway

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

What is the cheapest time of day to fly from KY to MDW?

Find hourly flight availability from Kentucky to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

When flying from Kentucky to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 21, 2024.
Read through reviews of airlines operating flights from Kentucky to Chicago, such as Southwest, Frontier and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

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
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

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
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

Reviews

1 / 10

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

Frontier
6.1
Okay
3,536 reviews
Southwest
8.1
Very good
5,005 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Entertainment

7.7

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 Kentucky to Midway. 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 Kentucky to Chicago Midway Airport 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 $58 and Allegiant Air from $77 one-way.

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

    When deciding which route to take from Kentucky to Chicago Midway Airport consider Nashville Intl - Chicago Midway, Cincinnati Cinci./N. Kentucky - Chicago Midway or Knoxville McGhee Tyson - Chicago Midway as they are the most popular.

  • What are the cheapest flights from Kentucky to Chicago Midway Airport?

    Looking at all options, your cheapest flight can be booked for $81. While the most popular route (Nashville Intl - Chicago Midway) can be booked for $98 on average our data indicates $333 when flying from Kentucky to Chicago Midway Airport.

  • Can I find deals for flights from Kentucky to Midway that include hotel bookings?

    Yes. In addition to deals on Kentucky to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kentucky to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Midway.

  • Can I find deals for business class flights from Kentucky to Midway?

    Yes. Cheapflights offers flight deals from Kentucky to Midway 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 Kentucky to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Kentucky to Chicago Midway Airport (average of $160). Flying from Kentucky to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 Kentucky to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Burbank to O'Hare Intl flights
LaGuardia to Midway flights
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San Francisco to Midway flights
Seattle to Midway flights
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Minneapolis to Midway flights
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Dulles Intl to Midway flights
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Top 2 airlines flying from Kentucky to Midway

Discover the top 2 airlines that operate flights from Kentucky to Midway. 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$135Average$277FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$282FlexibilityNo cancel feeOn-time63%
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