Southwest® flights from San Antonio to Chicago-Midway from $183

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Low fares from San Antonio to Chicago-Midway

$

San Antonio (SAT)to

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

One-way

Basic

From
$183
Seen: 22 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$183
Seen: 19 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 10/13/2026

One-way

Basic

From
$183
Seen: 13 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 11/02/2026

One-way

Basic

From
$183
Seen: 11 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/07/2026

One-way

Basic

From
$183
Seen: 5 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$183
Seen: 5 hrs ago

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Explore flights from San Antonio to Chicago-Midway

Sep 2026
From$268*
Seen: 11 hrs ago
One Way/Basic
Oct 2026
From$183*
Seen: 12 hrs ago
One Way/Basic
Nov 2026
From$183*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $183
cmp-daily-histogram-bars-legend-max-price-aria-label $340
Displaying fares for September-2026
  • SAT–MDW, 09/11/2026: From $306
    11

    Fri

    SEP

  • SAT–MDW, 09/12/2026: From $278
    12

    Sat

  • SAT–MDW, 09/13/2026: From $306
    13

    Sun

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

    Mon

  • SAT–MDW, 09/15/2026: From $268
    15

    Tue

  • SAT–MDW, 09/16/2026: From $268
    16

    Wed

  • SAT–MDW, 09/17/2026: From $296
    17

    Thu

  • SAT–MDW, 09/18/2026: From $301
    18

    Fri

  • SAT–MDW, 09/19/2026: From $268
    19

    Sat

  • SAT–MDW, 09/20/2026: From $340
    20

    Sun

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Mon

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

    Tue

  • SAT–MDW, 09/23/2026: From $268
    23

    Wed

  • SAT–MDW, 09/24/2026: From $292
    24

    Thu

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

    Fri

  • SAT–MDW, 09/26/2026: From $268
    26

    Sat

  • SAT–MDW, 09/27/2026: From $337
    27

    Sun

  • SAT–MDW, 09/28/2026: From $292
    28

    Mon

  • SAT–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Tue

  • SAT–MDW, 09/30/2026: From $268
    30

    Wed

  • SAT–MDW, 10/01/2026: From $193
    01

    Thu

    OCT

  • SAT–MDW, 10/02/2026: From $204
    02

    Fri

  • SAT–MDW, 10/03/2026: From $183
    03

    Sat

  • SAT–MDW, 10/04/2026: From $274
    04

    Sun

  • SAT–MDW, 10/05/2026: From $183
    05

    Mon

  • SAT–MDW, 10/06/2026: From $183
    06

    Tue

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

    Wed

  • SAT–MDW, 10/08/2026: From $326
    08

    Thu

  • SAT–MDW, 10/09/2026: From $272
    09

    Fri

  • SAT–MDW, 10/10/2026: From $193
    10

    Sat

    • Range$183-$340

    *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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