Southwest® flights from Louisville to Chicago (Midway) from $119

Promo Code

Low fares from Louisville to Chicago (Midway)

$

Louisville (SDF)to

Chicago (Midway) (MDW)
Depart: 09/12/2026

One-way

Basic

From
$119
Seen: 22 hrs ago

Louisville (SDF)to

Chicago (Midway) (MDW)
Depart: 10/17/2026

One-way

Basic

From
$119
Seen: 17 hrs ago

Louisville (SDF)to

Chicago (Midway) (MDW)
Depart: 10/01/2026

One-way

Basic

From
$119
Seen: 19 hrs ago

Louisville (SDF)to

Chicago (Midway) (MDW)
Depart: 10/20/2026

One-way

Basic

From
$119
Seen: 13 hrs ago

Louisville (SDF)to

Chicago (Midway) (MDW)
Depart: 10/19/2026

One-way

Basic

From
$119
Seen: 9 hrs ago

Louisville (SDF)to

Chicago (Midway) (MDW)
Depart: 10/22/2026

One-way

Basic

From
$119
Seen: 6 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Louisville to Chicago (Midway)

Aug 2026
From$251*
Seen: 8 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 22 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $282
Displaying fares for August-2026
  • SDF–MDW, 08/21/2026: From $282
    21

    Fri

    AUG

  • SDF–MDW, 08/22/2026: From $251
    22

    Sat

  • SDF–MDW, 08/23/2026: From $282
    23

    Sun

  • SDF–MDW, 08/24/2026: From $282
    24

    Mon

  • SDF–MDW, 08/25/2026: From $251
    25

    Tue

  • SDF–MDW, 08/26/2026: From $251
    26

    Wed

  • SDF–MDW, 08/27/2026: From $282
    27

    Thu

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Fri

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

  • SDF–MDW, 08/30/2026: From $282
    30

    Sun

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • SDF–MDW, 09/04/2026: From $227
    04

    Fri

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

  • SDF–MDW, 09/11/2026: From $129
    11

    Fri

  • SDF–MDW, 09/12/2026: From $119
    12

    Sat

  • SDF–MDW, 09/13/2026: From $185
    13

    Sun

  • SDF–MDW, 09/14/2026: From $119
    14

    Mon

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    15

    Tue

  • SDF–MDW, 09/16/2026: From $119
    16

    Wed

  • SDF–MDW, 09/17/2026: From $119
    17

    Thu

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Fri

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

    • Range$119-$282

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Louisville International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 15 minutes
    Distance:
    271 miles

    Route Information

    75† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 2‡ Nonstop flights on Saturday
    • 3‡ Nonstop flights on Sunday

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    The average flight time from Louisville to Chicago (Midway) is 1 hour 15 minutes.
    There are 75 weekly flights from Louisville to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Louisville to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Louisville to Chicago (Midway) 2 times per day on Saturdays and 3 times per day on Sundays.
    To find the lowest fares by day and time to fly Louisville to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Louisville to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

    Explore Flights from Other Popular Origins

    Popular Flights from Louisville