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: 12/10/2026

One-way

Basic

From
$99
Seen: 20 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 11/12/2026

One-way

Basic

From
$99
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 12/31/2026

One-way

Basic

From
$99
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 10/24/2026

One-way

Basic

From
$99
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 11/17/2026

One-way

Basic

From
$99
Seen: 2 hrs ago

Chicago-Midway (MDW)to

Louisville (SDF)
Depart: 12/05/2026

One-way

Basic

From
$99
Seen: 1 hour ago

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Explore flights from Chicago-Midway to Louisville

Oct 2026
From$99*
Seen: 13 hrs ago
One Way/Basic
Nov 2026
From$99*
Seen: 17 hrs ago
One Way/Basic
Dec 2026
From$99*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $99
cmp-daily-histogram-bars-legend-max-price-aria-label $302
Displaying fares for October-2026
  • MDW–SDF, 10/01/2026: From $302
    01

    Thu

    OCT

  • MDW–SDF, 10/02/2026: From $302
    02

    Fri

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

    Sat

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    04

    Sun

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    05

    Mon

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    06

    Tue

  • MDW–SDF, 10/07/2026: From $271
    07

    Wed

  • MDW–SDF, 10/08/2026: From $302
    08

    Thu

  • MDW–SDF, 10/09/2026: From $302
    09

    Fri

  • MDW–SDF, 10/10/2026: From $271
    10

    Sat

  • MDW–SDF, 10/11/2026: From $302
    11

    Sun

  • MDW–SDF, 10/12/2026: From $302
    12

    Mon

  • MDW–SDF, 10/13/2026: From $271
    13

    Tue

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

    Wed

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

    Thu

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

    Fri

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    17

    Sat

  • MDW–SDF, 10/18/2026: From $247
    18

    Sun

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

    Mon

  • MDW–SDF, 10/20/2026: From $247
    20

    Tue

  • MDW–SDF, 10/21/2026: From $99
    21

    Wed

  • MDW–SDF, 10/22/2026: From $99
    22

    Thu

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

    Fri

  • MDW–SDF, 10/24/2026: From $99
    24

    Sat

  • MDW–SDF, 10/25/2026: From $205
    25

    Sun

  • MDW–SDF, 10/26/2026: From $99
    26

    Mon

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

    Tue

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

    Wed

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

    Thu

  • MDW–SDF, 10/30/2026: From $116
    30

    Fri

  • MDW–SDF, 10/31/2026: From $99
    31

    Sat

    • Range$99-$302

    *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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