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

Promo Code

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

$

Chicago (Midway) (MDW)to

San Jose, CA (SJC)
Depart: 09/05/2026

One-way

Basic

From
$119
Seen: 8 minutes ago

Chicago (Midway) (MDW)to

San Jose, CA (SJC)
Depart: 09/06/2026

One-way

Basic

From
$129
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

San Jose, CA (SJC)
Depart: 09/05/2026

One-way

Choice

From
$169
Seen: 8 minutes ago

Chicago (Midway) (MDW)to

San Jose, CA (SJC)
Depart: 09/06/2026

One-way

Choice

From
$179
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

San Jose, CA (SJC)
Depart: 10/07/2026

One-way

Basic

From
$185
Seen: 18 hrs ago

Chicago (Midway) (MDW)to

San Jose, CA (SJC)
Depart: 10/26/2026

One-way

Basic

From
$185
Seen: 10 hrs ago

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

Aug 2026
From$185*
Seen: 1 hour ago
One Way/Basic
Sep 2026
From$119*
Seen: 8 minutes ago
One Way/Basic
Oct 2026
From$185*
Seen: 3 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $185
cmp-daily-histogram-bars-legend-max-price-aria-label $665
Displaying fares for August-2026
  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    02

    Sun

    AUG

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    03

    Mon

  • MDW–SJC, 08/04/2026: From $665
    04

    Tue

  • MDW–SJC, 08/05/2026: From $665
    05

    Wed

  • MDW–SJC, 08/06/2026: From $665
    06

    Thu

  • MDW–SJC, 08/07/2026: From $665
    07

    Fri

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

    Sat

  • MDW–SJC, 08/09/2026: From $379
    09

    Sun

  • MDW–SJC, 08/10/2026: From $369
    10

    Mon

  • MDW–SJC, 08/11/2026: From $369
    11

    Tue

  • MDW–SJC, 08/12/2026: From $369
    12

    Wed

  • MDW–SJC, 08/13/2026: From $369
    13

    Thu

  • MDW–SJC, 08/14/2026: From $369
    14

    Fri

  • MDW–SJC, 08/15/2026: From $284
    15

    Sat

  • MDW–SJC, 08/16/2026: From $294
    16

    Sun

  • MDW–SJC, 08/17/2026: From $284
    17

    Mon

  • MDW–SJC, 08/18/2026: From $284
    18

    Tue

  • MDW–SJC, 08/19/2026: From $284
    19

    Wed

  • MDW–SJC, 08/20/2026: From $284
    20

    Thu

  • MDW–SJC, 08/21/2026: From $284
    21

    Fri

  • MDW–SJC, 08/22/2026: From $185
    22

    Sat

  • MDW–SJC, 08/23/2026: From $234
    23

    Sun

  • MDW–SJC, 08/24/2026: From $185
    24

    Mon

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    25

    Tue

  • MDW–SJC, 08/26/2026: From $185
    26

    Wed

  • MDW–SJC, 08/27/2026: From $185
    27

    Thu

  • MDW–SJC, 08/28/2026: From $197
    28

    Fri

  • MDW–SJC, 08/29/2026: From $185
    29

    Sat

  • MDW–SJC, 08/30/2026: From $229
    30

    Sun

  • MDW–SJC, 08/31/2026: From $185
    31

    Mon

  • MDW–SJC, 09/01/2026: From $185
    01

    Tue

    SEP

    • Range$185-$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:
    Chicago Midway International Airport
    Arriving at:
    Norman Y. Mineta San José International Airport
    Average flight time:
    4 hours 30 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 Chicago (Midway) to San Jose, CA is 4 hours 30 minutes.
    There are 156 weekly flights from Chicago (Midway) to San Jose, CA on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to San Jose, CA once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to San Jose, CA once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to San Jose, CA with Southwest, check out our Low Fare Calendar.
    You can rent a car at Norman Y. Mineta San José International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to San Jose, CA—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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