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Cheap flights from Chicago Midway Airport to Louisville from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Louisville departing on 9/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Louisville

Cheap round-trip flights

Southwest Logo
10:05 am - 12:25 pmMDW-SDF
1h 20mnonstop
Southwest Logo
7:10 pm - 7:30 pmSDF-MDW
1h 20mnonstop
$97Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 23
Southwest Logo
10:05 am - 12:25 pmMDW-SDF
1h 20mnonstop
Southwest Logo
3:50 pm - 8:25 pmSDF-MDW
5h 35m1 stop
$107Southwest
Find Deal
Tue, Sep 23 - Tue, Sep 23
Southwest Logo
4:35 pm - 12:10 amMDW-SDF
6h 35m2 stops
Southwest Logo
6:55 pm - 7:10 pmSDF-MDW
1h 15mnonstop
$112Southwest
Find Deal
Mon, Oct 6 - Wed, Oct 8
Southwest Logo
5:35 am - 1:00 pmMDW-SDF
6h 25m1 stop
Southwest Logo
5:30 am - 12:00 pmSDF-MDW
7h 30m1 stop
$117Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
5:35 am - 1:00 pmMDW-SDF
6h 25m1 stop
Southwest Logo
1:00 pm - 5:05 pmSDF-MDW
5h 05m2 stops
$122Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
10:10 am - 12:25 pmMDW-SDF
1h 15mnonstop
Southwest Logo
11:55 am - 12:10 pmSDF-MDW
1h 15mnonstop
$126Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Delta Logo
6:00 am - 11:43 amMDW-SDF
4h 43m1 stop
Delta Logo
6:00 pm - 9:36 pmSDF-MDW
4h 36m1 stop
$177Delta
Find Deal
Tue, Sep 23 - Tue, Sep 23
Delta Logo
9:20 am - 3:49 pmMDW-SDF
5h 29m1 stop
Delta Logo
6:00 am - 12:35 pmSDF-MDW
7h 35m2 stops
$182Delta
Find Deal
Wed, Jan 28 - Tue, Feb 3
Delta Logo
9:20 am - 5:42 pmMDW-SDF
7h 22m2 stops
Delta Logo
6:00 am - 12:35 pmSDF-MDW
7h 35m2 stops
$187Delta
Find Deal
Wed, Jan 28 - Tue, Feb 3
Logo
8:05 am - 5:55 pmMDW-SDF
8h 50m2 stops
Logo
9:14 am - 4:50 pmSDF-MDW
8h 36m1 stop
$273
Find Deal
Wed, Oct 8 - Thu, Oct 9

Southwest flights from Chicago Midway Airport to Louisville

Our best Southwest deals on Chicago Midway Airport to Louisville flight tickets
Southwest
Sep 23
MDW10:05 amChicago Midway
1h 20m
SDF12:25 pmLouisville Intl
Sep 23
SDF7:10 pmLouisville Intl
1h 20m
MDW7:30 pmChicago Midway
$97
Find similar
Southwest
Sep 23
MDW10:05 amChicago Midway
1h 20m
SDF12:25 pmLouisville Intl
Sep 23
SDF3:50 pmLouisville Intl
5h 35m
1 stop
MDW8:25 pmChicago Midway
$107
Find similar
Southwest
Oct 6
MDW4:35 pmChicago Midway
6h 35m
2 stops
SDF12:10 amLouisville Intl
Oct 8
SDF6:55 pmLouisville Intl
1h 15m
MDW7:10 pmChicago Midway
$112
Find similar

Delta flights from Chicago Midway Airport to Louisville

Our best Delta deals on Chicago Midway Airport to Louisville flight tickets
Delta
Sep 23
MDW6:00 amChicago Midway
4h 43m
1 stop
SDF11:43 amLouisville Intl
Sep 23
SDF6:00 pmLouisville Intl
4h 36m
1 stop
MDW9:36 pmChicago Midway
$177
Find similar
Delta
Jan 28
MDW9:20 amChicago Midway
5h 29m
1 stop
SDF3:49 pmLouisville Intl
Feb 3
SDF6:00 amLouisville Intl
7h 35m
2 stops
MDW12:35 pmChicago Midway
$182
Find similar
Delta
Jan 28
MDW9:20 amChicago Midway
7h 22m
2 stops
SDF5:42 pmLouisville Intl
Feb 3
SDF6:00 amLouisville Intl
7h 35m
2 stops
MDW12:35 pmChicago Midway
$187
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Louisville 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, momondo users made 832,500 searches. Data last updated August 28, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Louisville that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 9/23

10:05 am-12:25 pm

Nonstop1h 20m

Louisville Intl

Tue 9/23

7:10 pm-7:30 pm

Nonstop1h 20m

$97

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 9/23

10:05 am-12:25 pm

Nonstop1h 20m

Louisville Intl

Tue 9/23

3:50 pm-8:25 pm

1 stop5h 35m

$107

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Mon 10/6

4:35 pm-12:10 am

2 stops6h 35m

Louisville Intl

Wed 10/8

6:55 pm-7:10 pm

Nonstop1h 15m

$112

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 10/15

5:35 am-1:00 pm

1 stop6h 25m

Louisville Intl

Wed 10/22

5:30 am-12:00 pm

1 stop7h 30m

$117

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 10/15

5:35 am-1:00 pm

1 stop6h 25m

Louisville Intl

Wed 10/22

1:00 pm-5:05 pm

2 stops5h 05m

$122

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 10/15

10:10 am-12:25 pm

Nonstop1h 15m

Louisville Intl

Wed 10/22

11:55 am-12:10 pm

Nonstop1h 15m

$126

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 9/23

6:00 am-11:43 am

1 stop4h 43m

Louisville Intl

Tue 9/23

6:00 pm-9:36 pm

1 stop4h 36m

$177

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 1/28

9:20 am-3:49 pm

1 stop5h 29m

Louisville Intl

Tue 2/3

6:00 am-12:35 pm

2 stops7h 35m

$182

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 1/28

9:20 am-5:42 pm

2 stops7h 22m

Louisville Intl

Tue 2/3

6:00 am-12:35 pm

2 stops7h 35m

$187

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Wed 10/8

8:05 am-5:55 pm

2 stops8h 50m

Louisville Intl

Thu 10/9

9:14 am-4:50 pm

1 stop8h 36m

$273

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Louisville from

How to get the cheapest flight ticket from Chicago Midway Airport to Louisville

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Louisville?

If you are unable to visit Louisville during the month of September, then departing from Chicago Midway Airport during the month June is also very affordable. Most momondo users find prices during this month for around $260.

What is the cheapest day to depart on your flight to Louisville?

On average, the least expensive day to fly to Louisville from Chicago Midway Airport is on a Saturday. momondo users have found tickets for Saturday departures for as low as $257. However, this price may fluctuate depending on the airline, the season, and holidays. Flights from Chicago Midway Airport to Louisville on a Monday will generally be more expensive and average around $552. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Louisville?

Our data shows that the cheapest Chicago Midway Airport to Louisville flights are usually those with departure times in the afternoon. Our users have found flights to Louisville in the afternoon for as low as $293. In the morning is when there is more demand to fly to Louisville, so prices are often more expensive at around $319 per ticket.

What is the cheapest Chicago Midway to Louisville Intl flight route?

Fly from Chicago Midway to Louisville Intl for the best Chicago Midway - Louisville Intl flight prices

What cabin class options are available on Chicago Midway to Louisville Intl flights?

There is only 1 cabin class available to choose from on Chicago Midway to Louisville Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Chicago Midway Airport to Louisville

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Louisville according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Louisville (MDW to SDF) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Louisville

Best Price Found

$52

Fastest flight time

1h 10m

Direct flights

Every day

Airports in Louisville

1 airport
The best one-way flight to Louisville from Chicago Midway Airport in the past 72 hours is $52. The best round-trip flight deal from Chicago Midway Airport to Louisville found on momondo in the last 72 hours is $151.
The fastest flight from Chicago Midway Airport to Louisville takes 1h 10m
Direct flights go from Chicago Midway Airport to Louisville every day.
There is 1 airport near Louisville: Louisville Intl (SDF)
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  • How far is Chicago Midway to Louisville Intl by plane?

    The distance between Chicago Midway and Louisville Intl is about 266.0 mi. By plane, this route typically takes 1h 10m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Louisville Intl Airport?

    Prices for flights from Chicago Midway Airport to Louisville Intl Airport refresh daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Louisville Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Louisville Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Louisville Intl Airport.

  • What documentation or ID do you need to fly to Louisville Intl Airport?

    The necessary travel and health documents for your Louisville Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Louisville?

  • What is the most popular airline from Chicago Midway Airport to Louisville?

Best airlines flying from Chicago Midway Airport to Louisville

Compare and see reviews for airlines that fly from Chicago Midway Airport to Louisville with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $124Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Louisville

    Southwest flies from Chicago Midway Airport to Louisville around 15 times per week, with 4,242 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago Midway Airport to Louisville in the last 72 hours was $124 (round-trip), much lower than the average airfare cost of $532 for Southwest flights on this route.

Traveling to a place near Louisville?

Book flights to Louisville if you plan to visit one of these locations
French Lick
Elizabethtown
Bardstown
West Baden Springs
Jeffersonville
Shepherdsville
New Albany
Corydon
Elizabeth
Charlestown
Springfield
Brandenburg
Georgetown

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Louisville?

Finding the right flight to Louisville from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Louisville quick and easy, saving you time and money.

Can I find flights from Chicago to Louisville with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Louisville flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Louisville?

momondo provides multiple filters to help you find the best flight to Louisville from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Louisville right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Louisville from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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