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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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — MDW
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
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 octubre 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Southwest)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

January

Average price

$184

Good round-trip deal

$326 or less

Good one-way deal

$169 or less
Provider with most accurate pricing for Louisville Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Louisville Intl-Chicago Midway flights.
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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. 20% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in October 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 octubre 30, 2025.

This Southwest deal was found by Cheapflights users on 10/29. 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.
jue. 12/46:45 amSDF - MDW
Nonstop1h 15mSouthwest
lun. 12/810:05 amMDW - SDF
Nonstop1h 25mSouthwest
Deal found 10/29$97
This Southwest deal was found by Cheapflights users on 10/28. 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.
sáb. 12/67:10 amSDF - MDW
Nonstop1h 20mSouthwest
lun. 12/88:50 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 10/28$134
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/37:15 amSDF - MDW
1 stop5h 40mDelta
lun. 12/85:29 pmMDW - SDF
1 stop4h 29mDelta
Deal found 10/29$157
This Delta deal was found by Cheapflights users on 10/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/242:22 pmSDF - MDW
1 stop4h 46mDelta
mar. 12/161:14 pmMDW - SDF
1 stop3h 22mDelta
Deal found 10/29$167

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 octubre 30, 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

jue. 12/4

11:45 am-8:45 pm

2 stops10h 00m

Chicago Midway

lun. 12/8

10:05 am-12:30 pm

Nonstop1h 25m

$112

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

sáb. 12/6

7:10 am-7:30 am

Nonstop1h 20m

Chicago Midway

lun. 12/8

8:50 pm-11:05 pm

Nonstop1h 15m

$134

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 12/23

5:35 pm-11:05 pm

1 stop6h 30m

Chicago Midway

mar. 12/30

9:30 am-11:45 am

Nonstop1h 15m

$144

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mié. 12/3

6:16 pm-11:47 pm

1 stop6h 31m

Chicago Midway

mar. 12/9

5:29 pm-11:59 pm

1 stop5h 30m

$157

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

lun. 12/15

6:16 pm-11:47 pm

1 stop6h 31m

Chicago Midway

mié. 12/17

1:14 pm-5:36 pm

1 stop3h 22m

$157

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

lun. 12/15

7:50 am-12:34 pm

1 stop5h 44m

Chicago Midway

mar. 12/16

1:14 pm-5:36 pm

1 stop3h 22m

$157

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mié. 1/7

6:45 am-7:10 am

Nonstop1h 25m

$49

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mié. 1/21

6:30 pm-6:45 pm

Nonstop1h 15m

$49

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 1/27

6:45 am-7:10 am

Nonstop1h 25m

$49

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

lun. 12/15

7:05 pm-7:20 pm

Nonstop1h 15m

$49

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 15 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 October.
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, January is the cheapest month in which you can book a flight from Louisville to Chicago Midway Airport (average of $73). Flying from Louisville to Chicago Midway Airport in May is currently the most expensive (average of $192). 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 octubre 30, 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 16% 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 October 26, 2025.

Travelers seeking maximum savings on their Louisville to Chicago Midway Airport flight should consider departing on Saturday at noon 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 octubre 30, 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
4,243 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

Entertainment

7.5

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 0 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 10h. The time it takes to get you to your destination can typically vary by up to . Louisville and Chicago Midway Airport are separated by a distance of 271 mi.

  • 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 63% 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 $355, our data shows the cheapest flight currently is $137. 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, January is the cheapest month in which you can book a flight from Louisville to Chicago Midway Airport (average of $73). Flying from Louisville to Chicago Midway Airport in May is currently the most expensive (average of $192). 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
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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$97Average$253FlexibilityNo cancel feeOn-time63%

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