Southwest® flights from San Diego to Chicago-Midway from $109

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Low fares from San Diego to Chicago-Midway

$

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$109
Seen: 12 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$109
Seen: 14 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$109
Seen: 20 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 01/21/2027

One-way

Basic

From
$109
Seen: 10 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 01/09/2027

One-way

Basic

From
$109
Seen: 9 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$109
Seen: 9 hrs ago

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Explore flights from San Diego to Chicago-Midway

Oct 2026
From$189*
Seen: 21 hrs ago
One Way/Basic
Nov 2026
From$109*
Seen: 17 hrs ago
One Way/Basic
Dec 2026
From$109*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $109
cmp-daily-histogram-bars-legend-max-price-aria-label $354
Displaying fares for October-2026
  • SAN–MDW, 10/31/2026: From $189
    31

    Sat

    OCT

  • SAN–MDW, 11/01/2026: From $189
    01

    Sun

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

    Mon

  • SAN–MDW, 11/03/2026: From $199
    03

    Tue

  • SAN–MDW, 11/04/2026: From $189
    04

    Wed

  • SAN–MDW, 11/05/2026: From $189
    05

    Thu

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

    Fri

  • SAN–MDW, 11/07/2026: From $189
    07

    Sat

  • SAN–MDW, 11/08/2026: From $189
    08

    Sun

  • SAN–MDW, 11/09/2026: From $189
    09

    Mon

  • SAN–MDW, 11/10/2026: From $189
    10

    Tue

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

    Wed

  • SAN–MDW, 11/12/2026: From $139
    12

    Thu

  • SAN–MDW, 11/13/2026: From $139
    13

    Fri

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Sat

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

    Sun

  • SAN–MDW, 11/16/2026: From $189
    16

    Mon

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Tue

  • SAN–MDW, 11/18/2026: From $139
    18

    Wed

  • SAN–MDW, 11/19/2026: From $189
    19

    Thu

  • SAN–MDW, 11/20/2026: From $189
    20

    Fri

  • SAN–MDW, 11/21/2026: From $119
    21

    Sat

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

  • SAN–MDW, 11/23/2026: From $109
    23

    Mon

  • SAN–MDW, 11/24/2026: From $159
    24

    Tue

  • SAN–MDW, 11/25/2026: From $119
    25

    Wed

  • SAN–MDW, 11/26/2026: From $109
    26

    Thu

  • SAN–MDW, 11/27/2026: From $159
    27

    Fri

  • SAN–MDW, 11/28/2026: From $354
    28

    Sat

  • SAN–MDW, 11/29/2026: From $322
    29

    Sun

  • SAN–MDW, 11/30/2026: From $189
    30

    Mon

    • Range$109-$354

    *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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