Southwest® flights from St. Louis to Chicago (O'Hare)

Promo Code

Low fares from St. Louis to Chicago (O'Hare)

$

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$59
Seen: 23 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 11/09/2026

One-way

Basic

From
$59
Seen: 13 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 11/12/2026

One-way

Basic

From
$59
Seen: 8 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 09/23/2026

One-way

Basic

From
$59
Seen: 12 hrs ago

St. Louis (STL)to

Chicago (Midway) (MDW)
Depart: 09/17/2026

One-way

Basic

From
$59
Seen: 4 hrs ago

St. Louis (STL)to

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

One-way

Basic

From
$59
Seen: 5 hrs ago

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Explore flights from St. Louis to Chicago (O'Hare)

Aug 2026
From$244*
Seen: 7 hrs ago
One Way/Basic
Sep 2026
From$59*
Seen: 22 hrs ago
One Way/Basic
Oct 2026
From$59*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $59
cmp-daily-histogram-bars-legend-max-price-aria-label $270
Displaying fares for August-2026
  • STL–MDW, 08/25/2026: From $244
    25

    Tue

    AUG

  • STL–MDW, 08/26/2026: From $244
    26

    Wed

  • STL–MDW, 08/27/2026: From $270
    27

    Thu

  • STL–MDW, 08/28/2026: From $270
    28

    Fri

  • STL–MDW, 08/29/2026: From $244
    29

    Sat

  • STL–MDW, 08/30/2026: From $270
    30

    Sun

  • STL–MDW, 08/31/2026: From $270
    31

    Mon

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

    Tue

    SEP

  • STL–MDW, 09/02/2026: From $244
    02

    Wed

  • STL–MDW, 09/03/2026: From $270
    03

    Thu

  • STL–MDW, 09/04/2026: From $270
    04

    Fri

  • STL–MDW, 09/05/2026: From $193
    05

    Sat

  • STL–MDW, 09/06/2026: From $193
    06

    Sun

  • STL–MDW, 09/07/2026: From $225
    07

    Mon

  • STL–MDW, 09/08/2026: From $225
    08

    Tue

  • STL–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • STL–MDW, 09/10/2026: From $193
    10

    Thu

  • STL–MDW, 09/11/2026: From $193
    11

    Fri

  • STL–MDW, 09/12/2026: From $193
    12

    Sat

  • STL–MDW, 09/13/2026: From $185
    13

    Sun

  • STL–MDW, 09/14/2026: From $59
    14

    Mon

  • STL–MDW, 09/15/2026: From $59
    15

    Tue

  • STL–MDW, 09/16/2026: From $59
    16

    Wed

  • STL–MDW, 09/17/2026: From $59
    17

    Thu

  • STL–MDW, 09/18/2026: From $76
    18

    Fri

  • STL–MDW, 09/19/2026: From $59
    19

    Sat

  • STL–MDW, 09/20/2026: From $185
    20

    Sun

  • STL–MDW, 09/21/2026: From $59
    21

    Mon

  • STL–MDW, 09/22/2026: From $59
    22

    Tue

  • STL–MDW, 09/23/2026: From $59
    23

    Wed

  • STL–MDW, 09/24/2026: From $59
    24

    Thu

    • Range$59-$270

    *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:
    O'Hare International Airport
    Distance:
    258 miles

    Route Information

    75† Weekly flights

    † 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

    There are 75 weekly flights from St. Louis to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly St. Louis to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from St. Louis to Chicago (O'Hare)—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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