Southwest® flights from Louisville to Chicago-Midway from $110

Promo Code

Low fares from Louisville to Chicago-Midway

$

Louisville (SDF)to

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

One-way

Basic

From
$110
Seen: 22 hrs ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 02/03/2027

One-way

Basic

From
$110
Seen: 3 hrs ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$110
Seen: 2 hrs ago

Louisville (SDF)to

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

One-way

Basic

From
$110
Seen: 1 hour ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$110
Seen: 18 hrs ago

Louisville (SDF)to

Chicago-Midway (MDW)
Depart: 01/09/2027

One-way

Basic

From
$110
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

Nov 2026
From$250*
Seen: 4 hrs ago
One Way/Basic
Dec 2026
From$110*
Seen: 18 hrs ago
One Way/Basic
Jan 2027
From$110*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $110
cmp-daily-histogram-bars-legend-max-price-aria-label $294
Displaying fares for November-2026
  • SDF–MDW, 11/10/2026: From $273
    10

    Tue

    NOV

  • SDF–MDW, 11/11/2026: From $273
    11

    Wed

  • SDF–MDW, 11/12/2026: From $273
    12

    Thu

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

    Fri

  • SDF–MDW, 11/14/2026: From $273
    14

    Sat

  • SDF–MDW, 11/15/2026: From $273
    15

    Sun

  • SDF–MDW, 11/16/2026: From $273
    16

    Mon

  • SDF–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • SDF–MDW, 11/18/2026: From $273
    18

    Wed

  • SDF–MDW, 11/19/2026: From $273
    19

    Thu

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

    Fri

  • SDF–MDW, 11/21/2026: From $273
    21

    Sat

  • SDF–MDW, 11/22/2026: From $273
    22

    Sun

  • SDF–MDW, 11/23/2026: From $262
    23

    Mon

  • SDF–MDW, 11/24/2026: From $262
    24

    Tue

  • SDF–MDW, 11/25/2026: From $294
    25

    Wed

  • SDF–MDW, 11/26/2026: From $262
    26

    Thu

  • SDF–MDW, 11/27/2026: From $262
    27

    Fri

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

    Sat

  • SDF–MDW, 11/29/2026: From $250
    29

    Sun

  • SDF–MDW, 11/30/2026: From $250
    30

    Mon

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

    Tue

    DEC

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

    Wed

  • SDF–MDW, 12/03/2026: From $125
    03

    Thu

  • SDF–MDW, 12/04/2026: From $135
    04

    Fri

  • SDF–MDW, 12/05/2026: From $110
    05

    Sat

  • SDF–MDW, 12/06/2026: From $220
    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

    • Range$110-$294

    *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

    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