Southwest® flights from Chicago (Midway) to San Antonio from $149

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Low fares from Chicago (Midway) to San Antonio

$

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 09/11/2026

One-way

Basic

From
$149
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 09/05/2026

One-way

Basic

From
$149
Seen: 7 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 10/30/2026

One-way

Basic

From
$149
Seen: 4 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 09/06/2026

One-way

Basic

From
$159
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 09/14/2026

One-way

Basic

From
$162
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 08/26/2026

One-way

Basic

From
$162
Seen: 15 hrs ago

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Explore flights from Chicago (Midway) to San Antonio

Aug 2026
From$162*
Seen: 15 hrs ago
One Way/Basic
Sep 2026
From$149*
Seen: 21 hrs ago
One Way/Basic
Oct 2026
From$149*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $162
cmp-daily-histogram-bars-legend-max-price-aria-label $371
Displaying fares for August-2026
  • MDW–SAT: cmp-view-offers-disclaimer. Find Offers
    03

    Mon

    AUG

  • MDW–SAT, 08/04/2026: From $268
    04

    Tue

  • MDW–SAT, 08/05/2026: From $258
    05

    Wed

  • MDW–SAT, 08/06/2026: From $286
    06

    Thu

  • MDW–SAT, 08/07/2026: From $286
    07

    Fri

  • MDW–SAT, 08/08/2026: From $268
    08

    Sat

  • MDW–SAT, 08/09/2026: From $371
    09

    Sun

  • MDW–SAT, 08/10/2026: From $286
    10

    Mon

  • MDW–SAT, 08/11/2026: From $258
    11

    Tue

  • MDW–SAT: cmp-view-offers-disclaimer. Find Offers
    12

    Wed

  • MDW–SAT: cmp-view-offers-disclaimer. Find Offers
    13

    Thu

  • MDW–SAT, 08/14/2026: From $286
    14

    Fri

  • MDW–SAT, 08/15/2026: From $258
    15

    Sat

  • MDW–SAT, 08/16/2026: From $282
    16

    Sun

  • MDW–SAT, 08/17/2026: From $282
    17

    Mon

  • MDW–SAT, 08/18/2026: From $258
    18

    Tue

  • MDW–SAT, 08/19/2026: From $258
    19

    Wed

  • MDW–SAT, 08/20/2026: From $282
    20

    Thu

  • MDW–SAT, 08/21/2026: From $282
    21

    Fri

  • MDW–SAT, 08/22/2026: From $258
    22

    Sat

  • MDW–SAT, 08/23/2026: From $264
    23

    Sun

  • MDW–SAT, 08/24/2026: From $162
    24

    Mon

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

    Tue

  • MDW–SAT, 08/26/2026: From $162
    26

    Wed

  • MDW–SAT, 08/27/2026: From $162
    27

    Thu

  • MDW–SAT, 08/28/2026: From $196
    28

    Fri

  • MDW–SAT, 08/29/2026: From $172
    29

    Sat

  • MDW–SAT, 08/30/2026: From $264
    30

    Sun

  • MDW–SAT, 08/31/2026: From $162
    31

    Mon

  • MDW–SAT, 09/01/2026: From $162
    01

    Tue

    SEP

  • MDW–SAT, 09/02/2026: From $162
    02

    Wed

    • Range$162-$371

    *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:
    Chicago Midway International Airport
    Arriving at:
    San Antonio International Airport
    Average flight time:
    2 hours 48 minutes
    Distance:
    1036 miles

    Route Information

    156† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 2‡ Nonstop flights on Saturday
    • 2‡ 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 Chicago (Midway) to San Antonio is 2 hours 48 minutes.
    There are 156 weekly flights from Chicago (Midway) to San Antonio on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to San Antonio 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to San Antonio 2 times per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to San Antonio with Southwest, check out our Low Fare Calendar.
    You can rent a car at San Antonio International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to San Antonio—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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