Southwest® flights from St. Louis to Chicago-Midway from $84

Promo Code

Low fares from St. Louis to Chicago-Midway

$

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 02/09/2027

One-way

Basic

From
$84
Seen: 17 hrs ago

St. Louis (STL)to

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

One-way

Basic

From
$84
Seen: 20 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 12/29/2026

One-way

Basic

From
$84
Seen: 10 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 01/27/2027

One-way

Basic

From
$84
Seen: 4 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$84
Seen: 13 hrs ago

St. Louis (STL)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$84
Seen: 11 hrs ago

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Explore flights from St. Louis to Chicago-Midway

Nov 2026
From$263*
Seen: 21 hrs ago
One Way/Basic
Dec 2026
From$84*
Seen: 13 hrs ago
One Way/Basic
Jan 2027
From$84*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $84
cmp-daily-histogram-bars-legend-max-price-aria-label $298
Displaying fares for November-2026
  • STL–MDW, 11/15/2026: From $263
    15

    Sun

    NOV

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

    Mon

  • STL–MDW, 11/17/2026: From $263
    17

    Tue

  • STL–MDW, 11/18/2026: From $263
    18

    Wed

  • STL–MDW, 11/19/2026: From $263
    19

    Thu

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

    Fri

  • STL–MDW, 11/21/2026: From $263
    21

    Sat

  • STL–MDW, 11/22/2026: From $263
    22

    Sun

  • STL–MDW, 11/23/2026: From $263
    23

    Mon

  • STL–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Tue

  • STL–MDW, 11/25/2026: From $298
    25

    Wed

  • STL–MDW, 11/26/2026: From $263
    26

    Thu

  • STL–MDW, 11/27/2026: From $263
    27

    Fri

  • STL–MDW, 11/28/2026: From $263
    28

    Sat

  • STL–MDW, 11/29/2026: From $263
    29

    Sun

  • STL–MDW, 11/30/2026: From $263
    30

    Mon

  • STL–MDW, 12/01/2026: From $263
    01

    Tue

    DEC

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

    Wed

  • STL–MDW, 12/03/2026: From $263
    03

    Thu

  • STL–MDW, 12/04/2026: From $263
    04

    Fri

  • STL–MDW, 12/05/2026: From $104
    05

    Sat

  • STL–MDW, 12/06/2026: From $225
    06

    Sun

  • STL–MDW, 12/07/2026: From $104
    07

    Mon

  • STL–MDW, 12/08/2026: From $84
    08

    Tue

  • STL–MDW, 12/09/2026: From $84
    09

    Wed

  • STL–MDW, 12/10/2026: From $104
    10

    Thu

  • STL–MDW, 12/11/2026: From $124
    11

    Fri

  • STL–MDW, 12/12/2026: From $127
    12

    Sat

  • STL–MDW, 12/13/2026: From $225
    13

    Sun

  • STL–MDW, 12/14/2026: From $104
    14

    Mon

    • Range$84-$298

    *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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