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Cheap flights from Louisville to Chicago from $90

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 9/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Louisville to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:55 pm - 5:15 pmSDF  Louisville Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
1:45 pm - 4:00 pmMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$199Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
4:55 pm - 5:15 pmSDF  Louisville Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
8:55 am - 2:30 pmMDW  Chicago Midway-SDF Louisville Intl
4h 35m1 stop Nashville Intl
$208Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
4:55 pm - 5:15 pmSDF  Louisville Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
6:15 pm - 8:30 pmMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$217Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
3:50 pm - 8:35 pmSDF  Louisville Intl-MDW Chicago Midway
5h 45m1 stop Baltimore/Washington
Southwest Logo
8:55 am - 2:30 pmMDW  Chicago Midway-SDF Louisville Intl
4h 35m1 stop Nashville Intl
$218Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
4:55 pm - 5:15 pmSDF  Louisville Intl-MDW Chicago Midway
1h 20mnonstop
Southwest Logo
1:00 pm - 3:15 pmMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
$226Southwest
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
2:15 pm - 2:30 pmSDF  Louisville Intl-MDW Chicago Midway
1h 15mnonstop
Southwest Logo
6:10 pm - 8:30 pmMDW  Chicago Midway-SDF Louisville Intl
1h 20mnonstop
$226Southwest
Fri, Sep 11 - Mon, Sep 14
Delta Logo
6:00 am - 10:03 amSDF  Louisville Intl-MDW Chicago Midway
5h 03m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:15 pm - 11:59 pmMDW  Chicago Midway-SDF Louisville Intl
5h 44m1 stop Atlanta Hartsfield-Jackson
$255Delta
Wed, Oct 14 - Mon, Oct 19
Delta Logo
6:00 am - 10:03 amSDF  Louisville Intl-MDW Chicago Midway
5h 03m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:59 am - 4:54 pmMDW  Chicago Midway-SDF Louisville Intl
4h 55m1 stop Atlanta Hartsfield-Jackson
$255Delta
Tue, Oct 13 - Tue, Oct 20
Delta Logo
12:40 pm - 4:47 pmSDF  Louisville Intl-MDW Chicago Midway
5h 07m1 stop Minneapolis St Paul
Delta Logo
5:15 pm - 11:59 pmMDW  Chicago Midway-SDF Louisville Intl
5h 44m1 stop Atlanta Hartsfield-Jackson
$255Delta
Tue, Oct 13 - Mon, Oct 19
Delta Logo
7:55 am - 12:47 pmSDF  Louisville Intl-MDW Chicago Midway
5h 52m1 stop Detroit Metropolitan Wayne County
Delta Logo
12:45 pm - 7:10 pmMDW  Chicago Midway-SDF Louisville Intl
5h 25m1 stop Atlanta Hartsfield-Jackson
$255Delta
Sat, Oct 17 - Tue, Oct 20

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Southwest flights from Louisville to Chicago Midway Airport

Our best Southwest deals on Louisville to Chicago Midway Airport flight tickets
Southwest
Sep 11
SDF7:10 pmLouisville Intl
1h 15m
MDW7:25 pmChicago Midway
Sep 14
MDW8:00 amChicago Midway
1h 25m
SDF10:25 amLouisville Intl
$194
Southwest
Oct 13
SDF7:10 pmLouisville Intl
1h 15m
MDW7:25 pmChicago Midway
Oct 17
MDW8:05 amChicago Midway
1h 15m
SDF10:20 amLouisville Intl
$196
Southwest
Sep 5
SDF4:55 pmLouisville Intl
1h 20m
MDW5:15 pmChicago Midway
Sep 6
MDW1:45 pmChicago Midway
1h 15m
SDF4:00 pmLouisville Intl
$199

Delta flights from Louisville to Chicago Midway Airport

Our best Delta deals on Louisville to Chicago Midway Airport flight tickets
Delta
Oct 13
SDF12:40 pmLouisville Intl
5h 07m
1 stop
MDW4:47 pmChicago Midway
Oct 19
MDW5:15 pmChicago Midway
5h 44m
1 stop
SDF11:59 pmLouisville Intl
$255
Delta
Aug 28
SDF7:55 amLouisville Intl
5h 44m
1 stop
MDW12:39 pmChicago Midway
Aug 31
MDW6:05 amChicago Midway
5h 16m
1 stop
SDF12:21 pmLouisville Intl
$288
Delta
Sep 10
SDF12:34 pmLouisville Intl
6h 45m
1 stop
MDW6:19 pmChicago Midway
Sep 11
MDW5:03 pmChicago Midway
3h 13m
1 stop
SDF9:16 pmLouisville Intl
$291

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 August 10, 2026.
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

Cheapest round-trip
Quickest round-trip

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 9/5

4:55 pm-5:15 pm

Nonstop1h 20m

Chicago Midway

Sun 9/6

1:45 pm-4:00 pm

Nonstop1h 15m

$199

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 9/5

4:55 pm-5:15 pm

Nonstop1h 20m

Chicago Midway

Sun 9/6

8:55 am-2:30 pm

1 stop4h 35m

$208

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 9/5

4:55 pm-5:15 pm

Nonstop1h 20m

Chicago Midway

Sun 9/6

6:15 pm-8:30 pm

Nonstop1h 15m

$217

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 9/5

3:50 pm-8:35 pm

1 stop5h 45m

Chicago Midway

Sun 9/6

8:55 am-2:30 pm

1 stop4h 35m

$218

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 9/5

4:55 pm-5:15 pm

Nonstop1h 20m

Chicago Midway

Tue 9/8

1:00 pm-3:15 pm

Nonstop1h 15m

$226

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Fri 9/11

2:15 pm-2:30 pm

Nonstop1h 15m

Chicago Midway

Mon 9/14

6:10 pm-8:30 pm

Nonstop1h 20m

$226

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Wed 10/14

6:00 am-10:03 am

1 stop5h 03m

Chicago Midway

Mon 10/19

5:15 pm-11:59 pm

1 stop5h 44m

$255

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Tue 10/13

6:00 am-10:03 am

1 stop5h 03m

Chicago Midway

Tue 10/20

10:59 am-4:54 pm

1 stop4h 55m

$255

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Tue 10/13

12:40 pm-4:47 pm

1 stop5h 07m

Chicago Midway

Mon 10/19

5:15 pm-11:59 pm

1 stop5h 44m

$255

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 10/17

7:55 am-12:47 pm

1 stop5h 52m

Chicago Midway

Tue 10/20

12:45 pm-7:10 pm

1 stop5h 25m

$255

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?

Prices are currently low for flights on this route.

Typical prices usually range from $269 to $315.
The lowest price recently found on this route was $199.

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

The month of February is, on average, the cheapest month to fly to Chicago Midway Airport from Louisville, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of February, then departing from Louisville during the month January is also very affordable. Most momondo users find prices during this month for around $175.

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

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Louisville. The lowest ticket price found for a Saturday departure recently was $386. 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, Sunday 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 $455.

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

Flying to Chicago Midway Airport from Louisville at noon is the least expensive time of day to depart. momondo users have found prices as low as $389 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $448. 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 to Chicago Midway Airport flights?

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

Can stopping save me money on Louisville to Chicago Midway Airport flights?

You could potentially save up to 33% on your flight if you consider stops on a Louisville to Chicago Midway Airport flight.

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

$184

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 $184. The best round-trip flight deal from Louisville to Chicago Midway Airport found on momondo in the last 72 hours is $335.
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

Frequently asked questions about flying from Louisville to Chicago Midway Airport

  • 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
4,216 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 14 Southwest flights for this route in a normal week, average airfare is usually $297 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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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