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Midway

$79+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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 December 15, 2025.

This Southwest deal was found by Cheapflights users on 12/13. 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 12/316:45 amSDF - MDW
Nonstop1h 15mSouthwest
Tue 1/67:55 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 12/13$173
This Southwest deal was found by Cheapflights users on 12/13. 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 12/316:45 amSDF - MDW
Nonstop1h 15mSouthwest
Sat 1/33:45 pmMDW - SDF
Nonstop1h 10mSouthwest
Deal found 12/13$257
This Delta deal was found by Cheapflights users on 12/13. 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 12/241:52 pmSDF - MDW
1 stop4h 34mDelta
Sat 1/36:08 pmMDW - SDF
1 stop3h 50mDelta
Deal found 12/13$277
This Southwest deal was found by Cheapflights users on 12/15. 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.
Mon 12/296:20 amSDF - MDW
Nonstop1h 15mSouthwest
Thu 1/110:00 amMDW - SDF
Nonstop1h 25mSouthwest
Deal found 12/15$299
This Southwest deal was found by Cheapflights users on 12/13. 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.
Sun 12/285:05 amSDF - MDW
1 stop4h 55mSouthwest
Wed 12/3110:00 amMDW - SDF
Nonstop1h 25mSouthwest
Deal found 12/13$309
This Southwest deal was found by Cheapflights users on 12/15. 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.
Wed 12/315:30 amSDF - MDW
1 stop5h 40mSouthwest
Fri 1/29:30 amMDW - SDF
Nonstop1h 15mSouthwest
Deal found 12/15$339

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 December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$171
(Southwest)

One-way from

$79
(Kiwi.com)

Popular in

February

Cheapest in

September

Average price

$266

Good round-trip deal

$298 or less

Good one-way deal

$255 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
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One-way flight from Louisville Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 15, 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

Thu 1/8

6:45 am-7:10 am

Nonstop1h 25m

Chicago Midway

Mon 1/12

10:00 am-12:15 pm

Nonstop1h 15m

$171

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 1/21

6:45 am-7:10 am

Nonstop1h 25m

Chicago Midway

Thu 1/22

10:00 am-12:15 pm

Nonstop1h 15m

$171

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/31

6:45 am-7:00 am

Nonstop1h 15m

Chicago Midway

Tue 1/6

7:55 pm-10:10 pm

Nonstop1h 15m

$173

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 1/17

8:55 am-4:25 pm

2 stops8h 30m

Chicago Midway

Mon 1/19

9:35 am-11:50 am

Nonstop1h 15m

$186

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 2/24

6:30 pm-6:45 pm

Nonstop1h 15m

$86

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 2/21

6:40 am-7:05 am

Nonstop1h 25m

$86

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 3/3

6:45 am-7:10 am

Nonstop1h 25m

$86

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 1/29

6:45 am-7:10 am

Nonstop1h 25m

$86

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 2/28

6:40 am-7:05 am

Nonstop1h 25m

$86

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 2/3

6:45 am-7:10 am

Nonstop1h 25m

$86

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 14 results
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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Louisville-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 month to book a flight from Louisville to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Louisville to Chicago Midway Airport (average of $77). Flying from Louisville to Chicago Midway Airport in November is currently the most expensive (average of $251). 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 December 15, 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 25% 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 December 13, 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. Saturday evenings 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 December 15, 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
7.9
Good
4,250 reviews

Crew

8.6

Overall

7.9

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Crew

8.6

Overall

7.9

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 25m. 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 64% 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 $338, our data shows the cheapest flight currently is $101. When looking at the most popular route, (Louisville Intl - Chicago Midway), you can expect to pay $171 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, September is the cheapest month in which you can book a flight from Louisville to Chicago Midway Airport (average of $77). Flying from Louisville to Chicago Midway Airport in November is currently the most expensive (average of $251). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$260FlexibilityNo cancel feeOn-time63%

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