Southwest® flights from San Diego to Chicago-Midway from $137

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Low fares from San Diego to Chicago-Midway

$

San Diego (SAN)to

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

One-way

Basic

From
$137
Seen: 19 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 11/16/2026

One-way

Basic

From
$137
Seen: 23 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 12/17/2026

One-way

Basic

From
$137
Seen: 18 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 11/18/2026

One-way

Basic

From
$137
Seen: 16 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$137
Seen: 15 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 01/23/2027

One-way

Basic

From
$137
Seen: 9 hrs ago

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Explore flights from San Diego to Chicago-Midway

Oct 2026
From$288*
Seen: 7 hrs ago
One Way/Basic
Nov 2026
From$137*
Seen: 16 hrs ago
One Way/Basic
Dec 2026
From$137*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $137
cmp-daily-histogram-bars-legend-max-price-aria-label $317
Displaying fares for October-2026
  • SAN–MDW, 10/20/2026: From $288
    20

    Tue

    OCT

  • SAN–MDW, 10/21/2026: From $288
    21

    Wed

  • SAN–MDW, 10/22/2026: From $317
    22

    Thu

  • SAN–MDW, 10/23/2026: From $317
    23

    Fri

  • SAN–MDW, 10/24/2026: From $288
    24

    Sat

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • SAN–MDW, 10/26/2026: From $317
    26

    Mon

  • SAN–MDW, 10/27/2026: From $288
    27

    Tue

  • SAN–MDW, 10/28/2026: From $288
    28

    Wed

  • SAN–MDW, 10/29/2026: From $317
    29

    Thu

  • SAN–MDW, 10/30/2026: From $317
    30

    Fri

  • SAN–MDW, 10/31/2026: From $288
    31

    Sat

  • SAN–MDW, 11/01/2026: From $317
    01

    Sun

    NOV

  • SAN–MDW, 11/02/2026: From $317
    02

    Mon

  • SAN–MDW, 11/03/2026: From $254
    03

    Tue

  • SAN–MDW, 11/04/2026: From $254
    04

    Wed

  • SAN–MDW, 11/05/2026: From $254
    05

    Thu

  • SAN–MDW, 11/06/2026: From $254
    06

    Fri

  • SAN–MDW, 11/07/2026: From $254
    07

    Sat

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

    Sun

  • SAN–MDW, 11/09/2026: From $137
    09

    Mon

  • SAN–MDW, 11/10/2026: From $147
    10

    Tue

  • SAN–MDW, 11/11/2026: From $147
    11

    Wed

  • SAN–MDW, 11/12/2026: From $137
    12

    Thu

  • SAN–MDW, 11/13/2026: From $166
    13

    Fri

  • SAN–MDW, 11/14/2026: From $153
    14

    Sat

  • SAN–MDW, 11/15/2026: From $166
    15

    Sun

  • SAN–MDW, 11/16/2026: From $137
    16

    Mon

  • SAN–MDW, 11/17/2026: From $137
    17

    Tue

  • SAN–MDW, 11/18/2026: From $137
    18

    Wed

  • SAN–MDW, 11/19/2026: From $199
    19

    Thu

    • Range$137-$317

    *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 Diego International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    4 hours 3 minutes
    Distance:
    1728 miles

    Questions we hear the most

    The average flight time from San Diego to Chicago (Midway) is 4 hours 3 minutes.
    There are 156 weekly flights from San Diego to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from San Diego to Chicago (Midway) 3 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from San Diego to Chicago (Midway) 2 times per day on Saturdays and 3 times per day on Sundays.
    To find the lowest fares by day and time to fly San Diego 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 Diego 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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