Southwest® flights from Chicago (Midway) to San Antonio from $129

Promo Code

Low fares from Chicago (Midway) to San Antonio

$

Chicago (Midway) (MDW)to

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

One-way

Basic

From
$129
Seen: 17 hrs ago

Chicago (Midway) (MDW)to

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

One-way

Basic

From
$129
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 09/17/2026

One-way

Basic

From
$129
Seen: 21 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 10/14/2026

One-way

Basic

From
$129
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 11/21/2026

One-way

Basic

From
$139
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

San Antonio (SAT)
Depart: 09/28/2026

One-way

Basic

From
$140
Seen: 21 hrs ago

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Explore flights from Chicago (Midway) to San Antonio

Aug 2026
From$258*
Seen: 12 hrs ago
One Way/Basic
Sep 2026
From$129*
Seen: 21 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $296
Displaying fares for August-2026
  • MDW–SAT, 08/23/2026: From $296
    23

    Sun

    AUG

  • MDW–SAT, 08/24/2026: From $286
    24

    Mon

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

    Tue

  • MDW–SAT, 08/26/2026: From $258
    26

    Wed

  • MDW–SAT, 08/27/2026: From $286
    27

    Thu

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

    Fri

  • MDW–SAT, 08/29/2026: From $258
    29

    Sat

  • MDW–SAT, 08/30/2026: From $286
    30

    Sun

  • MDW–SAT, 08/31/2026: From $286
    31

    Mon

  • MDW–SAT, 09/01/2026: From $258
    01

    Tue

    SEP

  • MDW–SAT, 09/02/2026: From $258
    02

    Wed

  • MDW–SAT, 09/03/2026: From $286
    03

    Thu

  • MDW–SAT, 09/04/2026: From $286
    04

    Fri

  • MDW–SAT, 09/05/2026: From $218
    05

    Sat

  • MDW–SAT, 09/06/2026: From $282
    06

    Sun

  • MDW–SAT, 09/07/2026: From $292
    07

    Mon

  • MDW–SAT, 09/08/2026: From $258
    08

    Tue

  • MDW–SAT, 09/09/2026: From $208
    09

    Wed

  • MDW–SAT, 09/10/2026: From $208
    10

    Thu

  • MDW–SAT, 09/11/2026: From $208
    11

    Fri

  • MDW–SAT, 09/12/2026: From $149
    12

    Sat

  • MDW–SAT, 09/13/2026: From $273
    13

    Sun

  • MDW–SAT, 09/14/2026: From $196
    14

    Mon

  • MDW–SAT, 09/15/2026: From $149
    15

    Tue

  • MDW–SAT, 09/16/2026: From $149
    16

    Wed

  • MDW–SAT, 09/17/2026: From $129
    17

    Thu

  • MDW–SAT, 09/18/2026: From $162
    18

    Fri

  • MDW–SAT, 09/19/2026: From $159
    19

    Sat

  • MDW–SAT, 09/20/2026: From $264
    20

    Sun

  • MDW–SAT, 09/21/2026: From $199
    21

    Mon

  • MDW–SAT, 09/22/2026: From $149
    22

    Tue

    • Range$129-$296

    *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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