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$49+ Cheap flights from Louisville (SDF) 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Louisville to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Louisville (SDF) 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 septiembre 16, 2025.

Round-trip from

$107
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

August

Average price

$211

Good round-trip deal

$238 or less

Good one-way deal

$178 or less
From Louisville Intl to Chicago Midway
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One-way flight from Louisville Intl to Chicago Midway
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Highest demand for flights based on searches. 22% potential increase in price ($79 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Louisville Intl to Chicago Midway.
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Price to beat on a one-way flight from Louisville Intl to Chicago Midway.
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Find flight deals from Louisville to Midway

Cheapest flights from Louisville to Midway
Explore the most affordable flight options available from Louisville to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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.
mar. 11/43:20 pmSDF - MDW
1 stop6h 45mSouthwest
jue. 11/67:15 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 9/15$107
This Southwest deal was found by Cheapflights users on 9/14. 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.
mar. 10/1411:55 amSDF - MDW
Nonstop1h 15mSouthwest
mar. 10/2112:30 pmMDW - SDF
1 stop8h 10mSouthwest
Deal found 9/14$113
This Southwest deal was found by Cheapflights users on 9/15. 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.
sáb. 11/81:10 pmSDF - MDW
1 stop6h 55mSouthwest
mié. 11/128:25 amMDW - SDF
2 stops7h 45mSouthwest
Deal found 9/15$122
This Southwest deal was found by Cheapflights users on 9/14. 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.
lun. 10/208:15 pmSDF - MDW
Nonstop1h 15mSouthwest
vie. 10/249:25 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 9/14$134
This Southwest deal was found by Cheapflights users on 9/15. 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.
sáb. 10/114:25 pmSDF - MDW
Nonstop1h 15mSouthwest
lun. 10/139:25 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 9/15$164
This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 11/116:00 amSDF - MDW
1 stop4h 52mDelta
mar. 11/115:34 pmMDW - SDF
1 stop5h 32mDelta
Deal found 9/15$177
This Delta deal was found by Cheapflights users on 9/14. 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.
mié. 10/296:00 amSDF - MDW
2 stops7h 28mDelta
mié. 11/55:09 pmMDW - SDF
1 stop5h 52mDelta
Deal found 9/14$182
This Delta deal was found by Cheapflights users on 9/15. 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.
vie. 11/146:00 amSDF - MDW
1 stop4h 52mDelta
lun. 11/1710:47 amMDW - SDF
1 stop7h 07mDelta
Deal found 9/15$184

Cheapflights Fare Finder

 
Customize your flight search to find flights from Louisville 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 septiembre 16, 2025.
Use the filters below to find and compare flights from Louisville to Chicago Midway Airport that are best for you.

Fly from

Louisville

Fly to

Midway

Route

Depart

Return

Price

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

sáb. 11/8

1:10 pm-7:05 pm

1 stop6h 55m

Chicago Midway

mié. 11/12

8:25 am-5:10 pm

2 stops7h 45m

$122

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 11/11

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

mar. 11/11

5:34 pm-12:06 am

1 stop5h 32m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

sáb. 10/18

3:00 pm-6:25 pm

1 stop4h 25m

Chicago Midway

mar. 10/21

5:04 pm-12:01 am

1 stop5h 57m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mié. 11/12

7:50 am-12:34 pm

1 stop5h 44m

Chicago Midway

sáb. 11/15

9:32 am-2:23 pm

1 stop3h 51m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

jue. 11/13

6:35 am-6:50 am

Nonstop1h 15m

Chicago Midway

dom. 11/16

9:30 am-11:45 am

Nonstop1h 15m

$196

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

sáb. 10/25

4:25 pm-4:40 pm

Nonstop1h 15m

Chicago Midway

dom. 10/26

8:25 pm-10:35 pm

Nonstop1h 10m

$196

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

vie. 10/10

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

lun. 10/13

9:25 pm-11:40 pm

Nonstop1h 15m

$201

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

vie. 11/14

6:00 am-10:10 pm

1 stop17h 10m

Chicago Midway

sáb. 11/15

11:36 am-11:45 pm

1 stop11h 09m

$203

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mié. 10/15

6:55 pm-7:10 pm

Nonstop1h 15m

$49

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

sáb. 10/18

4:25 pm-4:40 pm

Nonstop1h 15m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 results
1
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Best time to book a flight from Louisville to Midway

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

Cheapflights Insights

Everything you need to know about your flight from Louisville to Chicago Midway Airport

What is the cheapest month to book a flight from Louisville to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Louisville to Chicago Midway Airport (average of $160). Flying from Louisville 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 SDF to MDW?

Find hourly flight availability from Louisville 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 septiembre 16, 2025.

When flying from Louisville to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 11% versus a flight in the evening.

What is the cheapest day to fly from Louisville to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Louisville to Midway. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Louisville to Chicago Midway Airport flight should consider departing on Friday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 septiembre 16, 2025.
Peruse reviews from past customers who have flown with Southwest from Louisville to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Louisville to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Louisville to Chicago Midway?

    If you book a flight to Chicago Midway from Louisville, you will be flying from Louisville Intl, which is the city’s only airport. Louisville Intl (SDF) is located 5.3 mi from the center of Louisville. There are 2 flights from Louisville Intl to Chicago Midway per day from 1 airline.

  • How long is the flight from Louisville to Chicago Midway Airport?

    Airlines like Southwest and Delta fly from Louisville to Chicago Midway Airport in about 4h 52m. The time it takes to get you to your destination can typically vary by up to 2h 03m. Louisville and Chicago Midway Airport are separated by a distance of 271 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Louisville to Chicago Midway Airport round-trip?

    According to our current data, Southwest ($97), offers the cheapest pricing from Louisville to Chicago Midway Airport. Southwest is currently priced 65% below the average price you’ll pay for this route.

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

    While on average a flight from Louisville to Chicago Midway Airport is generally $263, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Louisville Intl - Chicago Midway), you can expect to pay $97 for that flight.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Louisville to Chicago Midway Airport (average of $160). Flying from Louisville 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top airline flying from Louisville to Midway

Discover the top airline that operate flights from Louisville 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$260FlexibilityNo cancel feeOn-time63%

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