Southwest® flights from San Diego to Chicago-Midway from $149

Promo Code

Low fares from San Diego to Chicago-Midway

$

San Diego (SAN)to

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

One-way

Basic

From
$149
Seen: 13 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$149
Seen: 13 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$149
Seen: 5 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$149
Seen: 10 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 01/12/2027

One-way

Basic

From
$149
Seen: 8 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 12/23/2026

One-way

Basic

From
$149
Seen: 3 hrs ago

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Explore flights from San Diego to Chicago-Midway

Oct 2026
From$153*
Seen: 16 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 13 hrs ago
One Way/Basic
Dec 2026
From$149*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $307
Displaying fares for October-2026
  • SAN–MDW, 10/11/2026: From $307
    11

    Sun

    OCT

  • SAN–MDW, 10/12/2026: From $307
    12

    Mon

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Tue

  • SAN–MDW, 10/14/2026: From $284
    14

    Wed

  • SAN–MDW, 10/15/2026: From $307
    15

    Thu

  • SAN–MDW, 10/16/2026: From $307
    16

    Fri

  • SAN–MDW, 10/17/2026: From $284
    17

    Sat

  • SAN–MDW, 10/18/2026: From $307
    18

    Sun

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

    Mon

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Tue

  • SAN–MDW, 10/21/2026: From $284
    21

    Wed

  • SAN–MDW, 10/22/2026: From $307
    22

    Thu

  • SAN–MDW, 10/23/2026: From $307
    23

    Fri

  • SAN–MDW, 10/24/2026: From $284
    24

    Sat

  • SAN–MDW, 10/25/2026: From $244
    25

    Sun

  • SAN–MDW, 10/26/2026: From $176
    26

    Mon

  • SAN–MDW, 10/27/2026: From $153
    27

    Tue

  • SAN–MDW, 10/28/2026: From $153
    28

    Wed

  • SAN–MDW, 10/29/2026: From $176
    29

    Thu

  • SAN–MDW, 10/30/2026: From $244
    30

    Fri

  • SAN–MDW, 10/31/2026: From $176
    31

    Sat

  • SAN–MDW, 11/01/2026: From $209
    01

    Sun

    NOV

  • SAN–MDW, 11/02/2026: From $176
    02

    Mon

  • SAN–MDW, 11/03/2026: From $163
    03

    Tue

  • SAN–MDW, 11/04/2026: From $163
    04

    Wed

  • SAN–MDW, 11/05/2026: From $176
    05

    Thu

  • SAN–MDW, 11/06/2026: From $179
    06

    Fri

  • SAN–MDW, 11/07/2026: From $176
    07

    Sat

  • SAN–MDW, 11/08/2026: From $209
    08

    Sun

  • SAN–MDW, 11/09/2026: From $176
    09

    Mon

  • SAN–MDW, 11/10/2026: From $149
    10

    Tue

    • Range$149-$307

    *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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