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

Promo Code

Low fares from Louisville to Chicago-Midway

$

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 12/21/2026

One-way

Basic

From
$99
Seen: 23 hrs ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 11/18/2026

One-way

Basic

From
$99
Seen: 19 hrs ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 10/31/2026

One-way

Basic

From
$99
Seen: 23 hrs ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 10/24/2026

One-way

Basic

From
$99
Seen: 7 hrs ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 11/02/2026

One-way

Basic

From
$99
Seen: 17 hrs ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$99
Seen: 5 hrs ago

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Explore flights from Louisville to Chicago-Midway

Oct 2026
From$99*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$99*
Seen: 8 hrs ago
One Way/Basic
Dec 2026
From$99*
Seen: 20 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
  • SDF–MDW, 10/01/2026: From $302
    01

    Thu

    OCT

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

    Fri

  • SDF–MDW, 10/03/2026: From $271
    03

    Sat

  • SDF–MDW, 10/04/2026: From $302
    04

    Sun

  • SDF–MDW, 10/05/2026: From $302
    05

    Mon

  • SDF–MDW, 10/06/2026: From $271
    06

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Sun

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Tue

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

    Wed

  • SDF–MDW, 10/15/2026: From $247
    15

    Thu

  • SDF–MDW, 10/16/2026: From $247
    16

    Fri

  • SDF–MDW, 10/17/2026: From $247
    17

    Sat

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

    Sun

  • SDF–MDW, 10/19/2026: From $247
    19

    Mon

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

    Tue

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

    Wed

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

    Thu

  • SDF–MDW, 10/23/2026: From $205
    23

    Fri

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

    Sat

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

    Sun

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

    Mon

  • SDF–MDW, 10/27/2026: From $99
    27

    Tue

  • SDF–MDW, 10/28/2026: From $99
    28

    Wed

  • SDF–MDW, 10/29/2026: From $99
    29

    Thu

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

    Fri

  • SDF–MDW, 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:
    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.

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