Southwest® flights from San Diego to Chicago-Midway from $174

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Low fares from San Diego to Chicago-Midway

$

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 12/26/2026

One-way

Basic

From
$174
Seen: 13 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$174
Seen: 5 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 01/26/2027

One-way

Basic

From
$174
Seen: 3 hrs ago

San Diego (SAN)to

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

One-way

Basic

From
$174
Seen: 2 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 12/19/2026

One-way

Basic

From
$174
Seen: 19 hrs ago

San Diego (SAN)to

Chicago-Midway (MDW)
Depart: 01/30/2027

One-way

Basic

From
$174
Seen: 8 hrs ago

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Explore flights from San Diego to Chicago-Midway

Nov 2026
From$194*
Seen: 15 hrs ago
One Way/Basic
Dec 2026
From$174*
Seen: 19 hrs ago
One Way/Basic
Jan 2027
From$174*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $174
cmp-daily-histogram-bars-legend-max-price-aria-label $359
Displaying fares for November-2026
  • SAN–MDW, 11/09/2026: From $194
    09

    Mon

    NOV

  • SAN–MDW, 11/10/2026: From $194
    10

    Tue

  • SAN–MDW, 11/11/2026: From $204
    11

    Wed

  • SAN–MDW, 11/12/2026: From $194
    12

    Thu

  • SAN–MDW, 11/13/2026: From $194
    13

    Fri

  • SAN–MDW, 11/14/2026: From $204
    14

    Sat

  • SAN–MDW, 11/15/2026: From $194
    15

    Sun

  • SAN–MDW, 11/16/2026: From $234
    16

    Mon

  • SAN–MDW, 11/17/2026: From $194
    17

    Tue

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

  • SAN–MDW, 11/19/2026: From $204
    19

    Thu

  • SAN–MDW, 11/20/2026: From $224
    20

    Fri

  • SAN–MDW, 11/21/2026: From $194
    21

    Sat

  • SAN–MDW, 11/22/2026: From $194
    22

    Sun

  • SAN–MDW: cmp-view-offers-disclaimer. Find Offers
    23

    Mon

  • SAN–MDW, 11/24/2026: From $194
    24

    Tue

  • SAN–MDW, 11/25/2026: From $194
    25

    Wed

  • SAN–MDW, 11/26/2026: From $194
    26

    Thu

  • SAN–MDW, 11/27/2026: From $224
    27

    Fri

  • SAN–MDW, 11/28/2026: From $359
    28

    Sat

  • SAN–MDW, 11/29/2026: From $296
    29

    Sun

  • SAN–MDW, 11/30/2026: From $194
    30

    Mon

  • SAN–MDW, 12/01/2026: From $190
    01

    Tue

    DEC

  • SAN–MDW, 12/02/2026: From $190
    02

    Wed

  • SAN–MDW, 12/03/2026: From $194
    03

    Thu

  • SAN–MDW, 12/04/2026: From $194
    04

    Fri

  • SAN–MDW, 12/05/2026: From $190
    05

    Sat

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

    Sun

  • SAN–MDW, 12/07/2026: From $194
    07

    Mon

  • SAN–MDW, 12/08/2026: From $174
    08

    Tue

    • Range$174-$359

    *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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