$49 Cheap Flights from Chicago (MDW) to Louisville (SDF)

View $49 flight on Tue, Aug 5, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Louisville Intl. Airport (SDF)

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Cheap Flights from Chicago to Louisville (MDW-SDF)

Prices were available within the past 7 days and start at $49 for one-way flights and $91 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Sep 16 - Tue, Sep 23
MDW
Chicago
SDF
Louisville
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Louisville, returning Tue, Sep 23, priced at $91 found 1 day ago
Southwest Airlines
Tue, Sep 16 - Tue, Sep 23
MDW
Chicago
SDF
Louisville
$94 Roundtrip, found 1 day ago
$94
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Louisville, returning Tue, Sep 23, priced at $94 found 1 day ago
Southwest Airlines
Tue, Aug 5 - Thu, Aug 7
MDW
Chicago
SDF
Louisville
$97 Roundtrip, found 6 hours ago
$97
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Tue, Aug 5 from Chicago to Louisville, returning Thu, Aug 7, priced at $97 found 6 hours ago
Southwest Airlines
Tue, Sep 16 - Tue, Sep 23
MDW
Chicago
SDF
Louisville
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Louisville, returning Tue, Sep 23, priced at $101 found 1 day ago
Southwest Airlines
Tue, Sep 16 - Tue, Sep 23
MDW
Chicago
SDF
Louisville
$104 Roundtrip, found 1 day ago
$104
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Louisville, returning Tue, Sep 23, priced at $104 found 1 day ago
Southwest Airlines
Tue, Sep 16 - Tue, Sep 23
MDW
Chicago
SDF
Louisville
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Louisville, returning Tue, Sep 23, priced at $106 found 1 day ago
Southwest Airlines
Tue, Sep 16 - Tue, Sep 23
MDW
Chicago
SDF
Louisville
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Louisville, returning Tue, Sep 23, priced at $109 found 1 day ago
Southwest Airlines
Tue, Sep 16 - Tue, Sep 23
MDW
Chicago
SDF
Louisville
$111 Roundtrip, found 1 day ago
$111
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Sep 16 from Chicago to Louisville, returning Tue, Sep 23, priced at $111 found 1 day ago
Southwest Airlines
Wed, Aug 6 - Sat, Aug 9
MDW
Chicago
SDF
Louisville
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Aug 6 from Chicago to Louisville, returning Sat, Aug 9, priced at $111 found 2 days ago
Delta
Thu, Aug 7 - Sat, Aug 9
MDW
Chicago
SDF
Louisville
$143 Roundtrip, found 2 days ago
$143
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Aug 7 from Chicago to Louisville, returning Sat, Aug 9, priced at $143 found 2 days ago

Find the cheapest month to fly from Chicago (MDW) to Louisville (SDF)

April is typically the cheapest month to fly

From $97 - $593 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Louisville (SDF)
Origin airport
Midway Intl.
Destination airport
Louisville Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$91
Distance
270 mi
Average flight time
2 hours 12 mins

Chicago to Louisville Flights

The cheapest times to fly from Chicago to Louisville

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Louisville are during the month of September. You can find some of the cheapest flights from Chicago to Louisville with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Louisville

Sunday is one of the best days to book for cheap flights from Chicago to Louisville: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Louisville

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Louisville in 2025. You can also book with separate airlines for your outbound and return journeys, from $49 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Louisville flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Louisville airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF) cost?
Pick up cheap return fares starting from $112 from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and United flight leaving MDW on August 5 2025 and touching down at SDF. The price was last updated on July 11 2025 and has not changed since.
What is the cheapest month to fly from MDW to SDF?
The cheapest flights from MDW to SDF are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF)?
Catch a nonstop flight with Southwest Airlines and fly straight from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF).
What is the cheapest airline that flies from MDW to SDF?
With prices as low as $46 for a one-way flight from MDW to SDF, Southwest Airlines is currently the cheapest airline flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on August 25 2025. Prices were last updated on July 11 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF)?
Every day on average, 2 direct flights operate from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF). Select the departure date that works for you.
What are the most popular departure times for flights from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF)?
More travelers fly between MDW and SDF at 10 AM than at any other time. Rather skip the crowds? Travel outside of rush hours and you're likely to save on your fare as well.
What day of the week has the most flights from MDW to SDF?
Friday offers the most flights from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF). Consider leaving on this day and you'll have the best chance of finding a departure that works with your plans.
What is the earliest flight from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF)?
Catch the earliest flight at around 10:00AM UTC-6, departing from Midway Intl. Airport (MDW). You'll be flying for around 1h 15m, touching down at Louisville Intl. Airport (SDF) at approximately 12:15PM UTC-5.
How long does it take to fly from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF)?
It usually takes 1 hour and 13 minutes to travel the 270 mi from MDW to SDF.
What is the best time to fly from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF)?
To avoid potential delays on the Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF) route, aim to fly before 3 PM. Departures after this hour are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Louisville from Midway Intl. Airport (MDW)?
If you're taking a direct flight from Midway Intl. Airport (MDW) to Louisville, Louisville Intl. Airport (SDF) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF) last-minute?
Booking your plane ticket from MDW to SDF shortly before your getaway is generally more expensive. But if you're flexible with your travel dates and times, you could score a cheap last-minute fare.
Is it cheaper to book a MDW to SDF flight and hotel package?
Booking a MDW to SDF flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Pick from our wide range of accommodations and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Louisville Intl. Airport (SDF)?
If you reserved your MDW to SDF flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

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