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Midway

$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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Round-trip from

$117
(Southwest)

One-way from

$55
(Trip.com)

Good round-trip deal

$372 or less

Good one-way deal

$195 or less
From Kentucky to Chicago Midway
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One-way flight from Kentucky to Chicago Midway
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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 January 21, 2025.

This Southwest deal was found by Cheapflights users on 1/20. 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 2/197:20 amBNA - MDW
Nonstop1h 35mSouthwest
Wed 2/268:40 pmMDW - BNA
Nonstop1h 30mSouthwest
Deal found 1/20$117
This Frontier deal was found by Cheapflights users on 1/20. 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 2/286:01 pmBNA - MDW
1 stop6h 16mFrontier
Mon 3/36:40 amMDW - BNA
1 stop6h 43mFrontier
Deal found 1/20$140
This Southwest deal was found by Cheapflights users on 1/21. 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.
Tue 4/112:55 pmSDF - MDW
Nonstop1h 15mSouthwest
Thu 4/39:50 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 1/21$167
This Booking.com deal was found by Cheapflights users on 1/21. 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.
Thu 2/66:00 amCVG - MDW
1 stop19h 17mFrontier
Sun 2/98:45 amMDW - CVG
1 stop12h 34mFrontier
Deal found 1/21$170
This Southwest deal was found by Cheapflights users on 1/21. 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 2/204:40 pmCVG - MDW
1 stop6h 20mSouthwest
Thu 2/276:25 amMDW - CVG
1 stop5h 10mSouthwest
Deal found 1/21$172
This Delta deal was found by Cheapflights users on 1/19. 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 2/116:15 amBNA - MDW
1 stop6h 50mDelta
Tue 2/115:05 pmMDW - BNA
1 stop5h 37mDelta
Deal found 1/19$173
This Delta deal was found by Cheapflights users on 1/21. 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 3/37:35 amSDF - MDW
1 stop6h 30mDelta
Wed 3/56:00 amMDW - SDF
1 stop4h 51mDelta
Deal found 1/21$177
This Delta deal was found by Cheapflights users on 1/21. 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 2/1110:31 amCVG - MDW
1 stop3h 34mDelta
Wed 2/126:00 amMDW - CVG
1 stop7h 09mDelta
Deal found 1/21$177
This Delta deal was found by Cheapflights users on 1/21. 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 2/46:36 amTYS - MDW
1 stop7h 06mDelta
Sat 2/85:05 pmMDW - TYS
1 stop4h 17mDelta
Deal found 1/21$199
This Frontier deal was found by Cheapflights users on 1/20. 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 4/104:31 pmTYS - MDW
1 stop8h 50mFrontier
Sun 4/136:40 amMDW - TYS
1 stop8h 06mFrontier
Deal found 1/20$210
This Delta deal was found by Cheapflights users on 1/20. 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 2/281:11 pmLEX - MDW
1 stop4h 09mDelta
Sun 3/22:08 pmMDW - LEX
1 stop6h 30mDelta
Deal found 1/20$237
This Delta deal was found by Cheapflights users on 1/21. 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 4/97:20 pmTRI - MDW
1 stop4h 01mDelta
Tue 4/1510:10 amMDW - TRI
1 stop7h 03mDelta
Deal found 1/21$269

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 2/19

7:20 am-8:55 am

Nonstop1h 35m

Chicago Midway

Wed 2/26

8:40 pm-10:10 pm

Nonstop1h 30m

$117

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Fri 2/28

6:01 pm-12:17 am

1 stop6h 16m

Chicago Midway

Mon 3/3

6:40 am-1:23 pm

1 stop6h 43m

$140

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 4/1

12:55 pm-1:10 pm

Nonstop1h 15m

Chicago Midway

Thu 4/3

9:50 pm-12:05 am

Nonstop1h 15m

$167

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 2/6

6:00 am-12:17 am

1 stop19h 17m

Chicago Midway

Sun 2/9

8:45 am-10:19 pm

1 stop12h 34m

$170

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 2/20

4:40 pm-10:00 pm

1 stop6h 20m

Chicago Midway

Thu 2/27

6:25 am-12:35 pm

1 stop5h 10m

$172

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 2/11

6:15 am-1:05 pm

1 stop6h 50m

Chicago Midway

Tue 2/11

5:05 pm-10:42 pm

1 stop5h 37m

$173

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Mon 3/3

7:35 am-1:05 pm

1 stop6h 30m

Chicago Midway

Wed 3/5

6:00 am-11:51 am

1 stop4h 51m

$177

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 2/11

10:31 am-1:05 pm

1 stop3h 34m

Chicago Midway

Tue 2/18

6:00 am-12:01 pm

1 stop5h 01m

$177

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Tue 2/4

6:36 am-12:42 pm

1 stop7h 06m

Chicago Midway

Sat 2/8

5:05 pm-10:22 pm

1 stop4h 17m

$199

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 4/10

4:31 pm-12:21 am

1 stop8h 50m

Chicago Midway

Sun 4/13

6:40 am-3:46 pm

1 stop8h 06m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 31 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 January 21, 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 January 21, 2025.
Read through reviews of airlines operating flights from Kentucky to Chicago, such as Delta, Southwest and Frontier. 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
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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
801 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

Boarding

8.2

Comfort

8.1

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 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 Cincinnati Cinci./N. Kentucky - Chicago Midway, Nashville Intl - Chicago Midway or Lexington Blue Grass - 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 $138. While the most popular route (Cincinnati Cinci./N. Kentucky - Chicago Midway) can be booked for $130 on average our data indicates $328 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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Dulles Intl to Midway flights
Hobby to Midway flights
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Detroit to O'Hare Intl 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 2,558,603 searches. Data last updated January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$135Average$326FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$156Average$282FlexibilityNo cancel feeOn-time63%
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