Southwest® flights from St. Louis to Chicago-Midway from $59

Promo Code

Low fares from St. Louis to Chicago-Midway

$

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 11/27/2026

One-way

Basic

From
$59
Seen: 22 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 12/25/2026

One-way

Basic

From
$59
Seen: 21 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 01/21/2027

One-way

Basic

From
$59
Seen: 15 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 01/22/2027

One-way

Basic

From
$59
Seen: 18 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 12/07/2026

One-way

Basic

From
$59
Seen: 19 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 01/19/2027

One-way

Basic

From
$59
Seen: 12 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.

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Explore flights from St. Louis to Chicago-Midway

Oct 2026
From$263*
Seen: 9 hrs ago
One Way/Basic
Nov 2026
From$59*
Seen: 12 hrs ago
One Way/Basic
Dec 2026
From$59*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $59
cmp-daily-histogram-bars-legend-max-price-aria-label $300
Displaying fares for October-2026
  • STL–MDW, 10/25/2026: From $300
    25

    Sun

    OCT

  • STL–MDW, 10/26/2026: From $300
    26

    Mon

  • STL–MDW, 10/27/2026: From $263
    27

    Tue

  • STL–MDW, 10/28/2026: From $263
    28

    Wed

  • STL–MDW, 10/29/2026: From $300
    29

    Thu

  • STL–MDW, 10/30/2026: From $300
    30

    Fri

  • STL–MDW, 10/31/2026: From $263
    31

    Sat

  • STL–MDW, 11/01/2026: From $300
    01

    Sun

    NOV

  • STL–MDW, 11/02/2026: From $300
    02

    Mon

  • STL–MDW, 11/03/2026: From $263
    03

    Tue

  • STL–MDW, 11/04/2026: From $263
    04

    Wed

  • STL–MDW, 11/05/2026: From $300
    05

    Thu

  • STL–MDW, 11/06/2026: From $300
    06

    Fri

  • STL–MDW, 11/07/2026: From $255
    07

    Sat

  • STL–MDW, 11/08/2026: From $255
    08

    Sun

  • STL–MDW, 11/09/2026: From $255
    09

    Mon

  • STL–MDW, 11/10/2026: From $255
    10

    Tue

  • STL–MDW, 11/11/2026: From $255
    11

    Wed

  • STL–MDW, 11/12/2026: From $255
    12

    Thu

  • STL–MDW, 11/13/2026: From $255
    13

    Fri

  • STL–MDW, 11/14/2026: From $59
    14

    Sat

  • STL–MDW, 11/15/2026: From $150
    15

    Sun

  • STL–MDW, 11/16/2026: From $59
    16

    Mon

  • STL–MDW, 11/17/2026: From $59
    17

    Tue

  • STL–MDW, 11/18/2026: From $59
    18

    Wed

  • STL–MDW, 11/19/2026: From $59
    19

    Thu

  • STL–MDW, 11/20/2026: From $215
    20

    Fri

  • STL–MDW, 11/21/2026: From $59
    21

    Sat

  • STL–MDW, 11/22/2026: From $150
    22

    Sun

  • STL–MDW, 11/23/2026: From $59
    23

    Mon

  • STL–MDW, 11/24/2026: From $59
    24

    Tue

    • Range$59-$300

    *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:
    Lambert-St Louis Int'l Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    1 hour 9 minutes
    Distance:
    251 miles

    Questions we hear the most

    The average flight time from St. Louis to Chicago (Midway) is 1 hour 9 minutes.
    There are 156 weekly flights from St. Louis to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from St. Louis to Chicago (Midway) 4 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from St. Louis to Chicago (Midway) 3 times per day on Saturdays and 4 times per day on Sundays.
    To find the lowest fares by day and time to fly St. Louis 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 St. Louis 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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