Southwest® flights from San Antonio to Chicago-Midway from $206

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Low fares from San Antonio to Chicago-Midway

$

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/08/2026

One-way

Basic

From
$206
Seen: 22 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 02/09/2027

One-way

Basic

From
$206
Seen: 16 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$206
Seen: 2 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 12/30/2026

One-way

Basic

From
$206
Seen: 18 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 01/16/2027

One-way

Basic

From
$206
Seen: 19 hrs ago

San Antonio (SAT)to

Chicago-Midway (MDW)
Depart: 02/10/2027

One-way

Basic

From
$206
Seen: 19 hrs ago

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Explore flights from San Antonio to Chicago-Midway

Nov 2026
From$293*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$206*
Seen: 19 hrs ago
One Way/Basic
Jan 2027
From$206*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $206
cmp-daily-histogram-bars-legend-max-price-aria-label $386
Displaying fares for November-2026
  • SAT–MDW, 11/13/2026: From $321
    13

    Fri

    NOV

  • SAT–MDW, 11/14/2026: From $293
    14

    Sat

  • SAT–MDW, 11/15/2026: From $321
    15

    Sun

  • SAT–MDW, 11/16/2026: From $321
    16

    Mon

  • SAT–MDW, 11/17/2026: From $293
    17

    Tue

  • SAT–MDW, 11/18/2026: From $298
    18

    Wed

  • SAT–MDW, 11/19/2026: From $326
    19

    Thu

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

    Fri

  • SAT–MDW, 11/21/2026: From $293
    21

    Sat

  • SAT–MDW, 11/22/2026: From $326
    22

    Sun

  • SAT–MDW, 11/23/2026: From $321
    23

    Mon

  • SAT–MDW, 11/24/2026: From $293
    24

    Tue

  • SAT–MDW, 11/25/2026: From $293
    25

    Wed

  • SAT–MDW, 11/26/2026: From $317
    26

    Thu

  • SAT–MDW, 11/27/2026: From $317
    27

    Fri

  • SAT–MDW, 11/28/2026: From $376
    28

    Sat

  • SAT–MDW, 11/29/2026: From $386
    29

    Sun

  • SAT–MDW, 11/30/2026: From $344
    30

    Mon

  • SAT–MDW, 12/01/2026: From $293
    01

    Tue

    DEC

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

    Wed

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

    Thu

  • SAT–MDW, 12/04/2026: From $251
    04

    Fri

  • SAT–MDW, 12/05/2026: From $206
    05

    Sat

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

    Sun

  • SAT–MDW, 12/07/2026: From $226
    07

    Mon

  • SAT–MDW, 12/08/2026: From $206
    08

    Tue

  • SAT–MDW, 12/09/2026: From $206
    09

    Wed

  • SAT–MDW, 12/10/2026: From $226
    10

    Thu

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

    Fri

  • SAT–MDW, 12/12/2026: From $206
    12

    Sat

    • Range$206-$386

    *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

    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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