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$107+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
May 30 — Jun 61
Sat 5/30
Sat 6/6
1 adult, Economy
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Cheap 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 April 30, 2026.

This Southwest deal was found by Cheapflights users on 4/25. 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.
Sat 5/308:40 am
SDF
-
MDW
Nonstop1h 20m
Southwest
Tue 6/212:50 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Deal found 4/25$241
This Southwest deal was found by Cheapflights users on 4/28. 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 5/267:15 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Tue 6/212:50 pm
MDW
-
SDF
Nonstop1h 15m
Southwest
Deal found 4/28$257
This Southwest deal was found by Cheapflights users on 4/27. 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 5/267:15 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Wed 5/273:00 pm
MDW
-
SDF
1 stop5h 05m
Southwest
Deal found 4/27$267
This Southwest deal was found by Cheapflights users on 4/26. 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 8/117:05 am
SDF
-
MDW
2 stops9h 20m
Southwest
Sat 8/157:40 am
MDW
-
SDF
2 stops8h 35m
Southwest
Deal found 4/26$271
This Southwest deal was found by Cheapflights users on 4/27. 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 6/18:40 am
SDF
-
MDW
Nonstop1h 20m
Southwest
Tue 6/97:45 am
MDW
-
SDF
Nonstop1h 20m
Southwest
Deal found 4/27$272
This Southwest deal was found by Cheapflights users on 4/25. 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.
Sat 5/303:15 pm
SDF
-
MDW
1 stop3h 10m
Southwest
Mon 6/13:50 pm
MDW
-
SDF
1 stop4h 55m
Southwest
Deal found 4/25$276
This Delta deal was found by Cheapflights users on 4/28. 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 5/197:50 am
SDF
-
MDW
1 stop5h 52m
Delta
Wed 5/209:22 am
MDW
-
SDF
1 stop3h 29m
Delta
Deal found 4/28$277
This Southwest deal was found by Cheapflights users on 4/29. 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 5/298:10 pm
SDF
-
MDW
Nonstop1h 15m
Southwest
Mon 6/17:45 am
MDW
-
SDF
Nonstop1h 10m
Southwest
Deal found 4/29$281

Find 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 April 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(Southwest)

One-way from

$107
(Kiwi.com)

Popular in

May

Cheapest in

September

Average price

$317

Good round-trip deal

$349 or less

Good one-way deal

$228 or less
Provider with most accurate pricing for Louisville Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Chicago Midway flights.
Search Deals
From Louisville Intl to Chicago Midway
Search Deals
One-way flight from Louisville Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 28% potential increase in price ($97 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Louisville Intl to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Louisville Intl to Chicago Midway.
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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 April 30, 2026.
Use the filters below to find and compare flights from Louisville to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 5/19

3:30 pm-3:45 pm

Nonstop1h 15m

Chicago Midway

Wed 5/20

8:00 am-2:45 pm

1 stop5h 45m

$267

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 6/4

3:35 pm-3:50 pm

Nonstop1h 15m

Chicago Midway

Wed 6/10

7:45 am-10:05 am

Nonstop1h 20m

$272
Quickest round-trip

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Mon 6/1

2:40 pm-2:55 pm

Nonstop1h 15m

Chicago Midway

Thu 6/4

12:45 pm-2:55 pm

Nonstop1h 10m

$287

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 5/28

3:40 pm-9:15 pm

1 stop6h 35m

Chicago Midway

Thu 6/4

7:45 am-10:05 am

Nonstop1h 20m

$291

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Fri 5/29

2:40 pm-2:55 pm

Nonstop1h 15m

Chicago Midway

Mon 6/1

3:50 pm-9:45 pm

1 stop4h 55m

$291

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Mon 6/1

5:25 pm-10:45 pm

2 stops6h 20m

Chicago Midway

Tue 6/9

11:25 am-9:40 pm

2 stops9h 15m

$302

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sun 5/24

6:00 am-2:55 pm

1 stop9h 55m

Chicago Midway

Mon 5/25

5:30 am-11:40 am

1 stop5h 10m

$306
Cheapest one-way
Quickest one-way

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sun 5/24

9:30 am-9:45 am

Nonstop1h 15m

$138

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 5/27

7:08 am-11:56 am

1 stop5h 48m

$139

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sun 5/24

7:50 am-12:42 pm

1 stop5h 52m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Compare providers for flights from Louisville to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Louisville to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Louisville-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Louisville-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Louisville-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Louisville-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Louisville-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 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 April 30, 2026.

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 9% versus a flight in the morning.

How much does it cost to fly round-trip from Louisville to Chicago Midway Airport?

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 April 30, 2026.
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
4,314 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 fly from Louisville to Chicago Midway Airport in about 1h 15m. The time it takes to get you to your destination is usually consistent. Louisville and Chicago Midway Airport are separated by a distance of 271 mi. All flights are typically nonstop.

  • 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 60% 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 $375, our data shows the cheapest flight currently is $138. When looking at the most popular route, (Louisville Intl - Chicago Midway), you can expect to pay $241 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.

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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$230FlexibilityNo cancel feeOn-time63%

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