Southwest® flights from Chicago-Midway to San Antonio from $209

Promo Code

Low fares from Chicago-Midway to San Antonio

$

Chicago-Midway (MDW)to

San Antonio (SAT)
Depart: 10/29/2026

One-way

Basic

From
$209
Seen: 23 hrs ago

Chicago-Midway (MDW)to

San Antonio (SAT)
Depart: 12/05/2026

One-way

Basic

From
$209
Seen: 22 hrs ago

Chicago-Midway (MDW)to

San Antonio (SAT)
Depart: 11/24/2026

One-way

Basic

From
$209
Seen: 18 hrs ago

Chicago-Midway (MDW)to

San Antonio (SAT)
Depart: 12/01/2026

One-way

Basic

From
$209
Seen: 10 hrs ago

Chicago-Midway (MDW)to

San Antonio (SAT)
Depart: 12/14/2026

One-way

Basic

From
$209
Seen: 12 hrs ago

Chicago-Midway (MDW)to

San Antonio (SAT)
Depart: 12/15/2026

One-way

Basic

From
$209
Seen: 12 hrs ago

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Explore flights from Chicago-Midway to San Antonio

Sep 2026
From$278*
Seen: 19 hrs ago
One Way/Basic
Oct 2026
From$209*
Seen: 21 hrs ago
One Way/Basic
Nov 2026
From$209*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $217
cmp-daily-histogram-bars-legend-max-price-aria-label $391
Displaying fares for September-2026
  • MDW–SAT, 09/12/2026: From $288
    12

    Sat

    SEP

  • MDW–SAT, 09/13/2026: From $329
    13

    Sun

  • MDW–SAT, 09/14/2026: From $306
    14

    Mon

  • MDW–SAT, 09/15/2026: From $278
    15

    Tue

  • MDW–SAT, 09/16/2026: From $278
    16

    Wed

  • MDW–SAT: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

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

    Fri

  • MDW–SAT, 09/19/2026: From $288
    19

    Sat

  • MDW–SAT, 09/20/2026: From $391
    20

    Sun

  • MDW–SAT, 09/21/2026: From $306
    21

    Mon

  • MDW–SAT, 09/22/2026: From $278
    22

    Tue

  • MDW–SAT, 09/23/2026: From $278
    23

    Wed

  • MDW–SAT, 09/24/2026: From $306
    24

    Thu

  • MDW–SAT, 09/25/2026: From $302
    25

    Fri

  • MDW–SAT: cmp-view-offers-disclaimer. Find Offers
    26

    Sat

  • MDW–SAT, 09/27/2026: From $316
    27

    Sun

  • MDW–SAT, 09/28/2026: From $302
    28

    Mon

  • MDW–SAT, 09/29/2026: From $278
    29

    Tue

  • MDW–SAT, 09/30/2026: From $278
    30

    Wed

  • MDW–SAT, 10/01/2026: From $302
    01

    Thu

    OCT

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

    Fri

  • MDW–SAT, 10/03/2026: From $217
    03

    Sat

  • MDW–SAT, 10/04/2026: From $284
    04

    Sun

  • MDW–SAT, 10/05/2026: From $217
    05

    Mon

  • MDW–SAT: cmp-view-offers-disclaimer. Find Offers
    06

    Tue

  • MDW–SAT, 10/07/2026: From $217
    07

    Wed

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

    Thu

  • MDW–SAT, 10/09/2026: From $284
    09

    Fri

  • MDW–SAT, 10/10/2026: From $217
    10

    Sat

  • MDW–SAT, 10/11/2026: From $247
    11

    Sun

    • Range$217-$391

    *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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