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Cheap flights from Louisville to Chicago from $39

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Louisville to Chicago departing on 10/29. 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 Louisville to Chicago

Cheap round-trip flights

Southwest Logo
6:55 pm - 7:10 pmSDF-MDW
1h 15mnonstop
Southwest Logo
8:35 pm - 10:45 pmMDW-SDF
1h 10mnonstop
$154Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 22
Southwest Logo
8:15 pm - 8:30 pmSDF-MDW
1h 15mnonstop
Southwest Logo
7:15 pm - 9:30 pmMDW-SDF
1h 15mnonstop
$158Southwest
Find Deal
Thu, Oct 30 - Thu, Nov 6
Southwest Logo
11:55 am - 12:10 pmSDF-MDW
1h 15mnonstop
Southwest Logo
2:45 pm - 11:35 pmMDW-SDF
7h 50m1 stop
$164Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 22
Southwest Logo
1:00 pm - 5:05 pmSDF-MDW
5h 05m2 stops
Southwest Logo
8:35 pm - 10:45 pmMDW-SDF
1h 10mnonstop
$169Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 22
Southwest Logo
4:25 pm - 4:40 pmSDF-MDW
1h 15mnonstop
Southwest Logo
2:20 pm - 12:15 amMDW-SDF
8h 55m1 stop
$170Southwest
Find Deal
Sat, Nov 1 - Thu, Nov 6
Southwest Logo
8:15 pm - 8:30 pmSDF-MDW
1h 15mnonstop
Southwest Logo
10:10 am - 12:25 pmMDW-SDF
1h 15mnonstop
$171Southwest
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Fri, Oct 24 - Tue, Oct 28
Delta Logo
6:35 am - 1:07 pmSDF-MDW
7h 32m1 stop
Delta Logo
5:34 pm - 12:06 amMDW-SDF
5h 32m1 stop
$177Delta
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Tue, Nov 11 - Tue, Nov 11
Southwest Logo
1:00 pm - 5:05 pmSDF-MDW
5h 05m2 stops
Southwest Logo
2:45 pm - 11:35 pmMDW-SDF
7h 50m1 stop
$179Southwest
Find Deal
Tue, Oct 21 - Wed, Oct 22
Southwest Logo
7:05 pm - 7:20 pmSDF-MDW
1h 15mnonstop
Southwest Logo
8:10 am - 3:55 pmMDW-SDF
6h 45m1 stop
$180Southwest
Find Deal
Sat, Nov 22 - Mon, Nov 24
Delta Logo
6:00 am - 12:34 pmSDF-MDW
7h 34m2 stops
Delta Logo
5:34 pm - 12:06 amMDW-SDF
5h 32m1 stop
$182Delta
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Tue, Nov 11 - Tue, Nov 11

Southwest flights from Louisville to Chicago Midway Airport

Our best Southwest deals on Louisville to Chicago Midway Airport flight tickets
Southwest
Oct 21
SDF6:55 pmLouisville Intl
1h 15m
MDW7:10 pmChicago Midway
Oct 22
MDW8:35 pmChicago Midway
1h 10m
SDF10:45 pmLouisville Intl
$154
Find similar
Southwest
Oct 30
SDF8:15 pmLouisville Intl
1h 15m
MDW8:30 pmChicago Midway
Nov 6
MDW7:15 pmChicago Midway
1h 15m
SDF9:30 pmLouisville Intl
$158
Find similar
Southwest
Oct 21
SDF11:55 amLouisville Intl
1h 15m
MDW12:10 pmChicago Midway
Oct 22
MDW2:45 pmChicago Midway
7h 50m
1 stop
SDF11:35 pmLouisville Intl
$164
Find similar

Delta flights from Louisville to Chicago Midway Airport

Our best Delta deals on Louisville to Chicago Midway Airport flight tickets
Delta
Nov 11
SDF6:35 amLouisville Intl
7h 32m
1 stop
MDW1:07 pmChicago Midway
Nov 11
MDW5:34 pmChicago Midway
5h 32m
1 stop
SDF12:06 amLouisville Intl
$177
Find similar
Delta
Nov 11
SDF6:00 amLouisville Intl
7h 34m
2 stops
MDW12:34 pmChicago Midway
Nov 11
MDW5:34 pmChicago Midway
5h 32m
1 stop
SDF12:06 amLouisville Intl
$182
Find similar
Delta
Nov 11
SDF6:00 amLouisville Intl
4h 52m
1 stop
MDW9:52 amChicago Midway
Nov 11
MDW5:34 pmChicago Midway
5h 32m
1 stop
SDF12:06 amLouisville Intl
$251
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Louisville to Chicago Midway Airport 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 September 30, 2025.
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

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 10/21

6:55 pm-7:10 pm

Nonstop1h 15m

Chicago Midway

Wed 10/22

8:35 pm-10:45 pm

Nonstop1h 10m

$154

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 10/30

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

Thu 11/6

7:15 pm-9:30 pm

Nonstop1h 15m

$158

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 10/21

11:55 am-12:10 pm

Nonstop1h 15m

Chicago Midway

Wed 10/22

2:45 pm-11:35 pm

1 stop7h 50m

$164

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 10/21

1:00 pm-5:05 pm

2 stops5h 05m

Chicago Midway

Wed 10/22

8:35 pm-10:45 pm

Nonstop1h 10m

$169

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 11/1

4:25 pm-4:40 pm

Nonstop1h 15m

Chicago Midway

Thu 11/6

2:20 pm-12:15 am

1 stop8h 55m

$170

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Fri 10/24

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

Tue 10/28

10:10 am-12:25 pm

Nonstop1h 15m

$171

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 11/11

6:35 am-1:07 pm

1 stop7h 32m

Chicago Midway

Tue 11/11

5:34 pm-12:06 am

1 stop5h 32m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 10/21

1:00 pm-5:05 pm

2 stops5h 05m

Chicago Midway

Wed 10/22

2:45 pm-11:35 pm

1 stop7h 50m

$179

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 11/22

7:05 pm-7:20 pm

Nonstop1h 15m

Chicago Midway

Mon 11/24

8:10 am-3:55 pm

1 stop6h 45m

$180

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 11/11

6:00 am-12:34 pm

2 stops7h 34m

Chicago Midway

Tue 11/11

5:34 pm-12:06 am

1 stop5h 32m

$182

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 Chicago from

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

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 typical price of a round-trip flight between Louisville and Chicago Midway Airport?

What is the cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Louisville, with most prices found around $186. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Louisville during the month January is also very affordable. Most momondo users find prices during this month for around $197.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Louisville. The lowest ticket price found for a Tuesday departure recently was $385. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Louisville because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $416.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Louisville in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $367 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $422. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

There is only 1 cabin class available to choose from on Louisville Intl to Chicago Midway 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 Louisville to Chicago Midway Airport

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

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

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

Best Price Found

$200

Fastest flight time

1h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Louisville in the past 72 hours is $200. The best round-trip flight deal from Louisville to Chicago Midway Airport found on momondo in the last 72 hours is $255.
The fastest flight from Louisville to Chicago Midway Airport takes 1h 15m
Direct flights go from Louisville to Chicago Midway Airport every day.
Search flight deals

  • How far is Louisville Intl to Chicago Midway by plane?

    A flight from Louisville Intl to Chicago Midway will travel around 266.0 mi. Flights usually cover this in 1h 15m, depending on flying conditions and air traffic around both airports.

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Louisville Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Louisville to Chicago Midway Airport

Compare and see reviews for airlines that fly from Louisville to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $97Free CancellationRating
8.0
4,245 reviews
Search Southwest flights

  • Southwest Flights From Louisville to Chicago Midway Airport

    Southwest flight deals from Louisville to Chicago Midway Airport start from $97 round-trip. Over the 5 Southwest flights for this route in a normal week, average airfare is usually $254 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Louisville.

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

momondo does allow users to show only those flights to Chicago from Louisville which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Louisville to Chicago.

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

Yes momondo offers price alerts on flights to Chicago from Louisville. 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.

An easier way to manage your Chicago Midway Airport trip

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