Southwest® flights from San Antonio to Chicago-Midway from $137

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Low fares from San Antonio to Chicago-Midway

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San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$137
Seen: 9 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/14/2026

One-way

Basic

From
$137
Seen: 12 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 01/11/2027

One-way

Basic

From
$137
Seen: 15 hrs ago

San Antonio (SAT)to

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

One-way

Basic

From
$137
Seen: 16 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 01/23/2027

One-way

Basic

From
$137
Seen: 21 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/24/2026

One-way

Basic

From
$137
Seen: 4 hrs ago

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Explore flights from San Antonio to Chicago-Midway

Oct 2026
From$288*
Seen: 10 hrs ago
One Way/Basic
Nov 2026
From$137*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$137*
Seen: 21 minutes ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $137
cmp-daily-histogram-bars-legend-max-price-aria-label $339
Displaying fares for October-2026
  • SAT–MDW, 10/23/2026: From $326
    23

    Fri

    OCT

  • SAT–MDW, 10/24/2026: From $288
    24

    Sat

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

    Sun

  • SAT–MDW, 10/26/2026: From $326
    26

    Mon

  • SAT–MDW, 10/27/2026: From $288
    27

    Tue

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

    Wed

  • SAT–MDW, 10/29/2026: From $316
    29

    Thu

  • SAT–MDW, 10/30/2026: From $316
    30

    Fri

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

  • SAT–MDW, 11/01/2026: From $316
    01

    Sun

    NOV

  • SAT–MDW, 11/02/2026: From $316
    02

    Mon

  • SAT–MDW, 11/03/2026: From $288
    03

    Tue

  • SAT–MDW, 11/04/2026: From $298
    04

    Wed

  • SAT–MDW, 11/05/2026: From $322
    05

    Thu

  • SAT–MDW, 11/06/2026: From $312
    06

    Fri

  • SAT–MDW, 11/07/2026: From $288
    07

    Sat

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sun

  • SAT–MDW, 11/09/2026: From $339
    09

    Mon

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

  • SAT–MDW, 11/11/2026: From $137
    11

    Wed

  • SAT–MDW, 11/12/2026: From $187
    12

    Thu

  • SAT–MDW, 11/13/2026: From $159
    13

    Fri

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

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

    Sun

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

    Mon

  • SAT–MDW, 11/17/2026: From $137
    17

    Tue

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

  • SAT–MDW, 11/19/2026: From $294
    19

    Thu

  • SAT–MDW, 11/20/2026: From $294
    20

    Fri

  • SAT–MDW, 11/21/2026: From $147
    21

    Sat

  • SAT–MDW, 11/22/2026: From $159
    22

    Sun

    • Range$137-$339

    *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:
    San Antonio International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 37 minutes
    Distance:
    1036 miles

    Questions we hear the most

    The average flight time from San Antonio to Chicago (Midway) is 2 hours 37 minutes.
    There are 156 weekly flights from San Antonio to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from San Antonio to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from San Antonio to Chicago (Midway) 2 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly San Antonio 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 San Antonio 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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