Southwest® flights from San Diego to Chicago-Midway from $129

Promo Code

Low fares from San Diego to Chicago-Midway

$

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 11/04/2026

One-way

Basic

From
$129
Seen: 14 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 10/27/2026

One-way

Basic

From
$129
Seen: 8 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 10/31/2026

One-way

Basic

From
$129
Seen: 10 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 10/28/2026

One-way

Basic

From
$129
Seen: 17 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 10/21/2026

One-way

Basic

From
$129
Seen: 33 minutes ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 11/14/2026

One-way

Basic

From
$129
Seen: 17 hrs ago

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Explore flights from San Diego to Chicago-Midway

Sep 2026
From$198*
Seen: 44 minutes ago
One Way/Basic
Oct 2026
From$129*
Seen: 17 hrs ago
One Way/Basic
Nov 2026
From$129*
Seen: 17 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $129
cmp-daily-histogram-bars-legend-max-price-aria-label $312
Displaying fares for September-2026
  • SAN–MDW, 09/30/2026: From $198
    30

    Wed

    SEP

  • SAN–MDW, 10/01/2026: From $312
    01

    Thu

  • SAN–MDW, 10/02/2026: From $228
    02

    Fri

  • SAN–MDW, 10/03/2026: From $198
    03

    Sat

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

  • SAN–MDW, 10/06/2026: From $198
    06

    Tue

  • SAN–MDW, 10/07/2026: From $198
    07

    Wed

  • SAN–MDW, 10/08/2026: From $228
    08

    Thu

  • SAN–MDW, 10/09/2026: From $228
    09

    Fri

  • SAN–MDW, 10/10/2026: From $198
    10

    Sat

  • SAN–MDW, 10/11/2026: From $228
    11

    Sun

  • SAN–MDW, 10/12/2026: From $228
    12

    Mon

  • SAN–MDW, 10/13/2026: From $198
    13

    Tue

  • SAN–MDW, 10/14/2026: From $198
    14

    Wed

  • SAN–MDW, 10/15/2026: From $228
    15

    Thu

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Fri

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

    Sat

  • SAN–MDW, 10/18/2026: From $228
    18

    Sun

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Mon

  • SAN–MDW, 10/20/2026: From $198
    20

    Tue

  • SAN–MDW, 10/21/2026: From $129
    21

    Wed

  • SAN–MDW, 10/22/2026: From $179
    22

    Thu

  • SAN–MDW, 10/23/2026: From $179
    23

    Fri

  • SAN–MDW, 10/24/2026: From $129
    24

    Sat

  • SAN–MDW, 10/25/2026: From $179
    25

    Sun

  • SAN–MDW, 10/26/2026: From $179
    26

    Mon

  • SAN–MDW, 10/27/2026: From $129
    27

    Tue

  • SAN–MDW, 10/28/2026: From $129
    28

    Wed

  • SAN–MDW, 10/29/2026: From $169
    29

    Thu

    • Range$129-$312

    *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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