Southwest® flights from San Francisco to Chicago (Midway) from $119

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Low fares from San Francisco to Chicago (Midway)

$

San Francisco (SFO)to

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

One-way

Basic

From
$119
Seen: 16 hrs ago

San Francisco (SFO)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$119
Seen: 13 hrs ago

San Francisco (SFO)to

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

One-way

Basic

From
$119
Seen: 9 hrs ago

San Francisco (SFO)to

Chicago (Midway) (MDW)
Depart: 10/19/2026

One-way

Basic

From
$119
Seen: 5 hrs ago

San Francisco (SFO)to

Chicago (Midway) (MDW)
Depart: 09/14/2026

One-way

Basic

From
$119
Seen: 7 hrs ago

San Francisco (SFO)to

Chicago (Midway) (MDW)
Depart: 10/17/2026

One-way

Basic

From
$119
Seen: 6 hrs ago

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Explore flights from San Francisco to Chicago (Midway)

Aug 2026
From$237*
Seen: 14 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $281
Displaying fares for August-2026
  • SFO–MDW, 08/22/2026: From $247
    22

    Sat

    AUG

  • SFO–MDW, 08/23/2026: From $271
    23

    Sun

  • SFO–MDW, 08/24/2026: From $271
    24

    Mon

  • SFO–MDW, 08/25/2026: From $237
    25

    Tue

  • SFO–MDW, 08/26/2026: From $237
    26

    Wed

  • SFO–MDW, 08/27/2026: From $271
    27

    Thu

  • SFO–MDW, 08/28/2026: From $271
    28

    Fri

  • SFO–MDW, 08/29/2026: From $237
    29

    Sat

  • SFO–MDW, 08/30/2026: From $271
    30

    Sun

  • SFO–MDW, 08/31/2026: From $271
    31

    Mon

  • SFO–MDW, 09/01/2026: From $237
    01

    Tue

    SEP

  • SFO–MDW, 09/02/2026: From $247
    02

    Wed

  • SFO–MDW, 09/03/2026: From $281
    03

    Thu

  • SFO–MDW, 09/04/2026: From $271
    04

    Fri

  • SFO–MDW, 09/05/2026: From $208
    05

    Sat

  • SFO–MDW, 09/06/2026: From $218
    06

    Sun

  • SFO–MDW, 09/07/2026: From $271
    07

    Mon

  • SFO–MDW, 09/08/2026: From $237
    08

    Tue

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

    Wed

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

    Thu

  • SFO–MDW, 09/11/2026: From $129
    11

    Fri

  • SFO–MDW, 09/12/2026: From $119
    12

    Sat

  • SFO–MDW, 09/13/2026: From $169
    13

    Sun

  • SFO–MDW, 09/14/2026: From $119
    14

    Mon

  • SFO–MDW, 09/15/2026: From $119
    15

    Tue

  • SFO–MDW, 09/16/2026: From $119
    16

    Wed

  • SFO–MDW, 09/17/2026: From $179
    17

    Thu

  • SFO–MDW, 09/18/2026: From $129
    18

    Fri

  • SFO–MDW, 09/19/2026: From $119
    19

    Sat

  • SFO–MDW, 09/20/2026: From $169
    20

    Sun

  • SFO–MDW, 09/21/2026: From $119
    21

    Mon

    • Range$119-$281

    *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 Francisco International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    4 hours 5 minutes
    Distance:
    1855 miles

    Route Information

    156† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 1‡ Nonstop flight 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 Francisco to Chicago (Midway) is 4 hours 5 minutes.
    There are 156 weekly flights from San Francisco to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from San Francisco to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from San Francisco to Chicago (Midway) once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly San Francisco 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 Francisco 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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