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$55+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Kentucky to Midway

Keep the following information in mind while searching for Kentucky to Midway flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$110
(Frontier)

One-way from

$55
(Frontier)

Popular in

March

Cheapest in

August

Average price

$258

Good round-trip deal

$364 or less

Good one-way deal

$186 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
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From Kentucky to Chicago Midway
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One-way flight from Kentucky to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 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 Kentucky to Chicago Midway.
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Price to beat on a one-way flight from Kentucky to Chicago Midway.
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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 February 20, 2025.

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.
Wed 4/26:00 pmBNA - MDW
1 stop6h 21mFrontier
Wed 4/96:45 amMDW - BNA
1 stop6h 22mFrontier
Deal found 2/19$110
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.
Mon 4/141:05 pmSDF - MDW
Nonstop1h 15mSouthwest
Thu 4/172:05 pmMDW - SDF
Nonstop1h 10mSouthwest
Deal found 2/20$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.
Thu 3/135:10 amBNA - MDW
Nonstop1h 40mSouthwest
Mon 3/179:45 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 2/20$117
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/187:10 amCVG - MDW
1 stop9h 03mFrontier
Wed 3/193:14 pmMDW - CVG
1 stop15h 09mFrontier
Deal found 2/19$140
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.
Thu 3/61:15 pmCVG - MDW
1 stop4h 50mSouthwest
Mon 3/102:35 pmMDW - CVG
2 stops8h 40mSouthwest
Deal found 2/19$142
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.
Sat 3/86:00 amSDF - MDW
1 stop5h 16mDelta
Tue 3/112:55 pmMDW - SDF
2 stops8h 02mDelta
Deal found 2/20$182
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.
Mon 3/106:21 amCVG - MDW
1 stop4h 24mDelta
Wed 3/129:25 amMDW - CVG
2 stops8h 41mDelta
Deal found 2/20$182
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/104:31 pmTYS - MDW
1 stop8h 50mFrontier
Sun 4/136:45 amMDW - TYS
1 stop8h 01mFrontier
Deal found 2/18$190
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 4/16:00 amLEX - MDW
1 stop4h 09mDelta
Sat 4/51:12 pmMDW - LEX
1 stop3h 08mDelta
Deal found 2/20$192
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 4/85:45 amTYS - MDW
1 stop4h 22mDelta
Tue 4/84:59 pmMDW - TYS
1 stop5h 43mDelta
Deal found 2/20$199
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.
Wed 3/266:10 amBNA - MDW
1 stop6h 26mDelta
Fri 3/282:55 pmMDW - BNA
1 stop6h 07mDelta
Deal found 2/19$243
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.
Fri 3/77:08 pmTRI - MDW
1 stop4h 12mDelta
Tue 3/116:00 amMDW - TRI
1 stop5h 16mDelta
Deal found 2/20$279

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 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Kentucky

Fly to

Midway

Route

Depart

Return

Price

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 4/2

6:00 pm-12:21 am

1 stop6h 21m

Chicago Midway

Wed 4/9

6:45 am-1:07 pm

1 stop6h 22m

$110

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Mon 4/14

1:05 pm-1:20 pm

Nonstop1h 15m

Chicago Midway

Mon 4/21

9:10 am-11:20 am

Nonstop1h 10m

$117

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 3/13

5:10 am-6:50 am

Nonstop1h 40m

Chicago Midway

Mon 3/17

9:45 pm-11:15 pm

Nonstop1h 30m

$117

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 3/18

7:10 am-3:13 pm

1 stop9h 03m

Chicago Midway

Wed 3/19

3:14 pm-7:23 am

1 stop15h 09m

$140

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 3/6

1:15 pm-5:05 pm

1 stop4h 50m

Chicago Midway

Mon 3/10

2:35 pm-12:15 am

2 stops8h 40m

$142

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 3/8

6:00 am-10:16 am

1 stop5h 16m

Chicago Midway

Tue 3/11

2:55 pm-11:57 pm

2 stops8h 02m

$182

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 3/10

6:21 am-9:45 am

1 stop4h 24m

Chicago Midway

Wed 3/12

9:25 am-7:06 pm

2 stops8h 41m

$182

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 4/10

4:31 pm-12:21 am

1 stop8h 50m

Chicago Midway

Sun 4/13

6:45 am-3:46 pm

1 stop8h 01m

$190

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Tue 4/8

5:45 am-9:07 am

1 stop4h 22m

Chicago Midway

Tue 4/8

4:59 pm-11:42 pm

1 stop5h 43m

$199

LexingtonChicago

LEX - MDW

LEXMDW

Lexington Blue Grass

Tue 4/1

7:30 am-12:36 pm

1 stop6h 06m

Chicago Midway

Sat 4/5

1:12 pm-5:20 pm

1 stop3h 08m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 32 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 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 November is currently the most expensive (average of $249). 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.

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 February 20, 2025.

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 February 20, 2025.
Read through reviews of airlines operating flights from Kentucky to Chicago, such as Southwest, Delta and Allegiant Air. 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
4,411 reviews

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

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

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

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

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

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

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

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

Entertainment

7.6

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

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 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 $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 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 Louisville Intl - 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 $124. While the most popular route (Nashville Intl - Chicago Midway) can be booked for $117 on average our data indicates $329 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 November is currently the most expensive (average of $249). 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

Traveling to a place near Kentucky?

Book flights to Kentucky if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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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LaGuardia to Midway flights
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Austin to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
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Santa Ana to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Reagan-National to Midway flights
Raleigh to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
Love Field to O'Hare Intl flights
Miami to O'Hare Intl flights
Seattle to Midway flights
Atlanta to Midway flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Denver to Midway flights
Hobby to Midway flights
Nashville to O'Hare Intl flights
Hartford to O'Hare Intl flights

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 2,558,603 searches. Data last updated February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$135Average$357FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$178Average$277FlexibilityNo cancel feeOn-time63%
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