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: 10/10/2026

One-way

Basic

From
$109
Seen: 17 hrs ago

San Diego (SAN)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$109
Seen: 6 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$109
Seen: 7 hrs ago

San Diego (SAN)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$109
Seen: 3 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$109
Seen: 4 hrs ago

San Diego (SAN)to

Chicago (Midway) (MDW)
Depart: 09/12/2026

One-way

Basic

From
$109
Seen: 15 hrs ago

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Explore flights from San Diego to Chicago (Midway)

Aug 2026
From$178*
Seen: 9 hrs ago
One Way/Basic
Sep 2026
From$109*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$109*
Seen: 15 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $109
cmp-daily-histogram-bars-legend-max-price-aria-label $218
Displaying fares for August-2026
  • SAN–MDW, 08/21/2026: From $218
    21

    Fri

    AUG

  • SAN–MDW, 08/22/2026: From $218
    22

    Sat

  • SAN–MDW, 08/23/2026: From $208
    23

    Sun

  • SAN–MDW, 08/24/2026: From $208
    24

    Mon

  • SAN–MDW, 08/25/2026: From $178
    25

    Tue

  • SAN–MDW, 08/26/2026: From $178
    26

    Wed

  • SAN–MDW, 08/27/2026: From $208
    27

    Thu

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Fri

  • SAN–MDW, 08/29/2026: From $178
    29

    Sat

  • SAN–MDW, 08/30/2026: From $208
    30

    Sun

  • SAN–MDW, 08/31/2026: From $208
    31

    Mon

  • SAN–MDW, 09/01/2026: From $178
    01

    Tue

    SEP

  • SAN–MDW, 09/02/2026: From $178
    02

    Wed

  • SAN–MDW, 09/03/2026: From $218
    03

    Thu

  • SAN–MDW, 09/04/2026: From $208
    04

    Fri

  • SAN–MDW, 09/05/2026: From $178
    05

    Sat

  • SAN–MDW, 09/06/2026: From $195
    06

    Sun

  • SAN–MDW, 09/07/2026: From $218
    07

    Mon

  • SAN–MDW, 09/08/2026: From $178
    08

    Tue

  • SAN–MDW, 09/09/2026: From $178
    09

    Wed

  • SAN–MDW, 09/10/2026: From $139
    10

    Thu

  • SAN–MDW, 09/11/2026: From $151
    11

    Fri

  • SAN–MDW, 09/12/2026: From $109
    12

    Sat

  • SAN–MDW, 09/13/2026: From $159
    13

    Sun

  • SAN–MDW, 09/14/2026: From $139
    14

    Mon

  • SAN–MDW, 09/15/2026: From $109
    15

    Tue

  • SAN–MDW, 09/16/2026: From $149
    16

    Wed

  • SAN–MDW, 09/17/2026: From $184
    17

    Thu

  • SAN–MDW, 09/18/2026: From $151
    18

    Fri

  • SAN–MDW, 09/19/2026: From $109
    19

    Sat

  • SAN–MDW, 09/20/2026: From $159
    20

    Sun

    • Range$109-$218

    *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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