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: 09/11/2026

One-way

Basic

From
$59
Seen: 21 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$59
Seen: 9 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$59
Seen: 3 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 10/26/2026

One-way

Basic

From
$64
Seen: 12 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 08/31/2026

One-way

Basic

From
$64
Seen: 7 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 08/24/2026

One-way

Basic

From
$76
Seen: 22 hrs ago

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Explore flights from St. Louis to Chicago (Midway)

Aug 2026
From$64*
Seen: 7 hrs ago
One Way/Basic
Sep 2026
From$59*
Seen: 21 hrs ago
One Way/Basic
Oct 2026
From$59*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $64
cmp-daily-histogram-bars-legend-max-price-aria-label $280
Displaying fares for August-2026
  • STL–MDW, 08/04/2026: From $244
    04

    Tue

    AUG

  • STL–MDW, 08/05/2026: From $244
    05

    Wed

  • STL–MDW, 08/06/2026: From $280
    06

    Thu

  • STL–MDW, 08/07/2026: From $270
    07

    Fri

  • STL–MDW, 08/08/2026: From $244
    08

    Sat

  • STL–MDW, 08/09/2026: From $270
    09

    Sun

  • STL–MDW, 08/10/2026: From $270
    10

    Mon

  • STL–MDW, 08/11/2026: From $244
    11

    Tue

  • STL–MDW, 08/12/2026: From $244
    12

    Wed

  • STL–MDW, 08/13/2026: From $270
    13

    Thu

  • STL–MDW, 08/14/2026: From $270
    14

    Fri

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

    Sat

  • STL–MDW, 08/16/2026: From $270
    16

    Sun

  • STL–MDW, 08/17/2026: From $225
    17

    Mon

  • STL–MDW, 08/18/2026: From $225
    18

    Tue

  • STL–MDW, 08/19/2026: From $225
    19

    Wed

  • STL–MDW, 08/20/2026: From $225
    20

    Thu

  • STL–MDW, 08/21/2026: From $225
    21

    Fri

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

    Sat

  • STL–MDW, 08/23/2026: From $225
    23

    Sun

  • STL–MDW, 08/24/2026: From $76
    24

    Mon

  • STL–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

  • STL–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

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

    Thu

  • STL–MDW, 08/28/2026: From $125
    28

    Fri

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

    Sat

  • STL–MDW, 08/30/2026: From $185
    30

    Sun

  • STL–MDW, 08/31/2026: From $64
    31

    Mon

  • STL–MDW, 09/01/2026: From $76
    01

    Tue

    SEP

  • STL–MDW, 09/02/2026: From $76
    02

    Wed

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

    Thu

    • Range$64-$280

    *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

    Route Information

    156† Weekly flights
    • 4‡ Nonstop flights per day Monday through Friday
    • 3‡ Nonstop flights on Saturday
    • 4‡ 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 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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