Southwest® flights from San Diego to Chicago (Midway) from $109

Promo Code

Low fares from San Diego to Chicago (Midway)

$

San Diego (SAN)to

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

One-way

Basic

From
$109
Seen: 17 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$109
Seen: 13 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$109
Seen: 14 hrs ago

San Diego (SAN)to

Chicago (Midway) (MDW)
Depart: 10/06/2026

One-way

Basic

From
$109
Seen: 15 hrs ago

San Diego (SAN)to

Chicago (Midway) (MDW)
Depart: 10/07/2026

One-way

Basic

From
$109
Seen: 17 hrs ago

San Diego (SAN)to

Chicago (Midway) (MDW)
Depart: 09/02/2026

One-way

Basic

From
$109
Seen: 13 hrs ago

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Explore flights from San Diego to Chicago (Midway)

Jul 2026
From$242*
Seen: 4 hrs ago
One Way/Basic
Aug 2026
From$109*
Seen: 17 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 7 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $109
cmp-daily-histogram-bars-legend-max-price-aria-label $287
Displaying fares for July-2026
  • SAN–MDW, 07/31/2026: From $242
    31

    Fri

    JUL

  • SAN–MDW, 08/01/2026: From $229
    01

    Sat

  • SAN–MDW, 08/02/2026: From $282
    02

    Sun

  • SAN–MDW, 08/03/2026: From $242
    03

    Mon

  • SAN–MDW, 08/04/2026: From $219
    04

    Tue

  • SAN–MDW, 08/05/2026: From $219
    05

    Wed

  • SAN–MDW, 08/06/2026: From $242
    06

    Thu

  • SAN–MDW, 08/07/2026: From $287
    07

    Fri

  • SAN–MDW, 08/08/2026: From $219
    08

    Sat

  • SAN–MDW, 08/09/2026: From $242
    09

    Sun

  • SAN–MDW, 08/10/2026: From $252
    10

    Mon

  • SAN–MDW, 08/11/2026: From $229
    11

    Tue

  • SAN–MDW, 08/12/2026: From $219
    12

    Wed

  • SAN–MDW, 08/13/2026: From $242
    13

    Thu

  • SAN–MDW, 08/14/2026: From $234
    14

    Fri

  • SAN–MDW, 08/15/2026: From $229
    15

    Sat

  • SAN–MDW, 08/16/2026: From $234
    16

    Sun

  • SAN–MDW, 08/17/2026: From $234
    17

    Mon

  • SAN–MDW, 08/18/2026: From $219
    18

    Tue

  • SAN–MDW, 08/19/2026: From $219
    19

    Wed

  • SAN–MDW, 08/20/2026: From $129
    20

    Thu

  • SAN–MDW, 08/21/2026: From $182
    21

    Fri

  • SAN–MDW, 08/22/2026: From $184
    22

    Sat

  • SAN–MDW, 08/23/2026: From $199
    23

    Sun

  • SAN–MDW, 08/24/2026: From $129
    24

    Mon

  • SAN–MDW, 08/25/2026: From $140
    25

    Tue

  • SAN–MDW, 08/26/2026: From $109
    26

    Wed

  • SAN–MDW, 08/27/2026: From $119
    27

    Thu

  • SAN–MDW, 08/28/2026: From $119
    28

    Fri

  • SAN–MDW, 08/29/2026: From $109
    29

    Sat

  • SAN–MDW, 08/30/2026: From $149
    30

    Sun

    • Range$109-$287

    *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

    Route Information

    156† Weekly flights
    • 3‡ Nonstop flights per day Monday through Friday
    • 2‡ Nonstop flights on Saturday
    • 3‡ 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 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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