Southwest® flights from Chicago-Midway to Louisville from $99

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Low fares from Chicago-Midway to Louisville

$

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 11/14/2026

One-way

Basic

From
$99
Seen: 17 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 11/03/2026

One-way

Basic

From
$99
Seen: 21 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 10/15/2026

One-way

Basic

From
$99
Seen: 23 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 11/26/2026

One-way

Basic

From
$99
Seen: 7 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 10/12/2026

One-way

Basic

From
$99
Seen: 2 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 10/21/2026

One-way

Basic

From
$99
Seen: 1 hour ago

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Explore flights from Chicago-Midway to Louisville

Sep 2026
From$237*
Seen: 6 hrs ago
One Way/Basic
Oct 2026
From$99*
Seen: 20 hrs ago
One Way/Basic
Nov 2026
From$99*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $99
cmp-daily-histogram-bars-legend-max-price-aria-label $292
Displaying fares for September-2026
  • MDW–SDF, 09/11/2026: From $292
    11

    Fri

    SEP

  • MDW–SDF, 09/12/2026: From $261
    12

    Sat

  • MDW–SDF, 09/13/2026: From $292
    13

    Sun

  • MDW–SDF: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • MDW–SDF, 09/15/2026: From $271
    15

    Tue

  • MDW–SDF: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

  • MDW–SDF, 09/17/2026: From $292
    17

    Thu

  • MDW–SDF, 09/18/2026: From $292
    18

    Fri

  • MDW–SDF, 09/19/2026: From $261
    19

    Sat

  • MDW–SDF, 09/20/2026: From $292
    20

    Sun

  • MDW–SDF: cmp-view-offers-disclaimer. Find Offers
    21

    Mon

  • MDW–SDF: cmp-view-offers-disclaimer. Find Offers
    22

    Tue

  • MDW–SDF: cmp-view-offers-disclaimer. Find Offers
    23

    Wed

  • MDW–SDF, 09/24/2026: From $237
    24

    Thu

  • MDW–SDF, 09/25/2026: From $237
    25

    Fri

  • MDW–SDF, 09/26/2026: From $237
    26

    Sat

  • MDW–SDF: cmp-view-offers-disclaimer. Find Offers
    27

    Sun

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

    Mon

  • MDW–SDF, 09/29/2026: From $237
    29

    Tue

  • MDW–SDF: cmp-view-offers-disclaimer. Find Offers
    30

    Wed

  • MDW–SDF, 10/01/2026: From $99
    01

    Thu

    OCT

  • MDW–SDF, 10/02/2026: From $117
    02

    Fri

  • MDW–SDF, 10/03/2026: From $99
    03

    Sat

  • MDW–SDF, 10/04/2026: From $195
    04

    Sun

  • MDW–SDF, 10/05/2026: From $99
    05

    Mon

  • MDW–SDF, 10/06/2026: From $99
    06

    Tue

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

    Wed

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

    Thu

  • MDW–SDF, 10/09/2026: From $117
    09

    Fri

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

    Sat

    • Range$99-$292

    *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:
    Chicago Midway International Airport
    Arriving at:
    Louisville International Airport
    Average flight time:
    1 hour 11 minutes
    Distance:
    271 miles

    Route Information

    92† Weekly flights
    • 3‡ 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 Chicago (Midway) to Louisville is 1 hour 11 minutes.
    There are 92 weekly flights from Chicago (Midway) to Louisville on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Louisville 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Louisville 2 times per day on Saturdays and 3 times per day on Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Louisville with Southwest, check out our Low Fare Calendar.
    You can rent a car at Louisville International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Louisville—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.

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