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

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Low fares from San Antonio to Chicago (Midway)

$

San Antonio (SAT)to

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

One-way

Basic

From
$129
Seen: 11 hrs ago

San Antonio (SAT)to

Chicago (Midway) (MDW)
Depart: 10/21/2026

One-way

Basic

From
$129
Seen: 5 hrs ago

San Antonio (SAT)to

Chicago (Midway) (MDW)
Depart: 11/07/2026

One-way

Basic

From
$129
Seen: 20 hrs ago

San Antonio (SAT)to

Chicago (Midway) (MDW)
Depart: 09/21/2026

One-way

Basic

From
$129
Seen: 34 minutes ago

San Antonio (SAT)to

Chicago (Midway) (MDW)
Depart: 09/28/2026

One-way

Basic

From
$129
Seen: 29 minutes ago

San Antonio (SAT)to

Chicago (Midway) (MDW)
Depart: 10/31/2026

One-way

Basic

From
$129
Seen: 30 minutes ago

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Explore flights from San Antonio to Chicago (Midway)

Aug 2026
From$258*
Seen: 7 hrs ago
One Way/Basic
Sep 2026
From$129*
Seen: 16 hrs ago
One Way/Basic
Oct 2026
From$129*
Seen: 14 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
  • SAT–MDW, 08/22/2026: From $258
    22

    Sat

    AUG

  • SAT–MDW, 08/23/2026: From $296
    23

    Sun

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

    Mon

  • SAT–MDW, 08/25/2026: From $258
    25

    Tue

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

    Wed

  • SAT–MDW, 08/27/2026: From $291
    27

    Thu

  • SAT–MDW, 08/28/2026: From $291
    28

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

    SEP

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

    Wed

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • SAT–MDW, 09/04/2026: From $282
    04

    Fri

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

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

    Sun

  • SAT–MDW, 09/07/2026: From $282
    07

    Mon

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

    Tue

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

    Wed

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

    Thu

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

  • SAT–MDW, 09/12/2026: From $129
    12

    Sat

  • SAT–MDW, 09/13/2026: From $264
    13

    Sun

  • SAT–MDW, 09/14/2026: From $129
    14

    Mon

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

    Tue

  • SAT–MDW, 09/16/2026: From $129
    16

    Wed

  • SAT–MDW, 09/17/2026: From $162
    17

    Thu

  • SAT–MDW, 09/18/2026: From $172
    18

    Fri

  • SAT–MDW, 09/19/2026: From $172
    19

    Sat

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

  • SAT–MDW, 09/21/2026: From $129
    21

    Mon

    • 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:
    San Antonio International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 37 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 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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