Southwest® flights from San Jose, CA to Chicago (Midway) from $119

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Low fares from San Jose, CA to Chicago (Midway)

$

San Jose, CA (SJC)to

Chicago (Midway) (MDW)
Depart: 10/05/2026

One-way

Basic

From
$119
Seen: 18 hrs ago

San Jose, CA (SJC)to

Chicago (Midway) (MDW)
Depart: 09/22/2026

One-way

Basic

From
$119
Seen: 17 hrs ago

San Jose, CA (SJC)to

Chicago (Midway) (MDW)
Depart: 09/28/2026

One-way

Basic

From
$119
Seen: 17 hrs ago

San Jose, CA (SJC)to

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

One-way

Basic

From
$119
Seen: 17 hrs ago

San Jose, CA (SJC)to

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

One-way

Basic

From
$119
Seen: 21 hrs ago

San Jose, CA (SJC)to

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

One-way

Basic

From
$119
Seen: 20 hrs ago

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Explore flights from San Jose, CA to Chicago (Midway)

Aug 2026
From$369*
Seen: 19 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 20 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 12 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $665
Displaying fares for August-2026
  • SJC–MDW, 08/21/2026: From $665
    21

    Fri

    AUG

  • SJC–MDW, 08/22/2026: From $665
    22

    Sat

  • SJC–MDW, 08/23/2026: From $665
    23

    Sun

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Mon

  • SJC–MDW, 08/25/2026: From $665
    25

    Tue

  • SJC–MDW, 08/26/2026: From $665
    26

    Wed

  • SJC–MDW, 08/27/2026: From $369
    27

    Thu

  • SJC–MDW, 08/28/2026: From $369
    28

    Fri

  • SJC–MDW, 08/29/2026: From $369
    29

    Sat

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

  • SJC–MDW, 08/31/2026: From $369
    31

    Mon

  • SJC–MDW, 09/01/2026: From $369
    01

    Tue

    SEP

  • SJC–MDW, 09/02/2026: From $369
    02

    Wed

  • SJC–MDW, 09/03/2026: From $294
    03

    Thu

  • SJC–MDW, 09/04/2026: From $294
    04

    Fri

  • SJC–MDW, 09/05/2026: From $284
    05

    Sat

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

    Sun

  • SJC–MDW, 09/07/2026: From $284
    07

    Mon

  • SJC–MDW, 09/08/2026: From $284
    08

    Tue

  • SJC–MDW, 09/09/2026: From $119
    09

    Wed

  • SJC–MDW, 09/10/2026: From $129
    10

    Thu

  • SJC–MDW, 09/11/2026: From $169
    11

    Fri

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

  • SJC–MDW, 09/13/2026: From $169
    13

    Sun

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • SJC–MDW, 09/15/2026: From $119
    15

    Tue

  • SJC–MDW, 09/16/2026: From $119
    16

    Wed

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

    Thu

  • SJC–MDW, 09/18/2026: From $169
    18

    Fri

  • SJC–MDW, 09/19/2026: From $119
    19

    Sat

  • SJC–MDW, 09/20/2026: From $169
    20

    Sun

    • Range$119-$665

    *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:
    Norman Y. Mineta San José International Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    4 hours 8 minutes
    Distance:
    1838 miles

    Route Information

    156† Weekly flights
    • 1‡ Nonstop flight per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 1‡ Nonstop flight 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 Jose, CA to Chicago (Midway) is 4 hours 8 minutes.
    There are 156 weekly flights from San Jose, CA to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from San Jose, CA to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from San Jose, CA to Chicago (Midway) once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly San Jose, CA 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 Jose, CA 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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