Southwest® flights from Chicago-Midway to San Jose, CA from $201

Promo Code

Low fares from Chicago-Midway to San Jose, CA

$

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 11/26/2026

One-way

Basic

From
$201
Seen: 18 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 12/05/2026

One-way

Basic

From
$201
Seen: 18 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$201
Seen: 18 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 10/02/2026

One-way

Basic

From
$201
Seen: 23 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 12/14/2026

One-way

Basic

From
$201
Seen: 20 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 10/17/2026

One-way

Basic

From
$201
Seen: 22 hrs ago

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Explore flights from Chicago-Midway to San Jose, CA

Sep 2026
From$304*
Seen: 21 hrs ago
One Way/Basic
Oct 2026
From$201*
Seen: 21 hrs ago
One Way/Basic
Nov 2026
From$201*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $201
cmp-daily-histogram-bars-legend-max-price-aria-label $685
Displaying fares for September-2026
  • MDW–SJC, 09/12/2026: From $685
    12

    Sat

    SEP

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

    Sun

  • MDW–SJC, 09/14/2026: From $685
    14

    Mon

  • MDW–SJC, 09/15/2026: From $685
    15

    Tue

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

    Wed

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

    Thu

  • MDW–SJC, 09/18/2026: From $389
    18

    Fri

  • MDW–SJC, 09/19/2026: From $389
    19

    Sat

  • MDW–SJC, 09/20/2026: From $389
    20

    Sun

  • MDW–SJC, 09/21/2026: From $389
    21

    Mon

  • MDW–SJC, 09/22/2026: From $389
    22

    Tue

  • MDW–SJC, 09/23/2026: From $389
    23

    Wed

  • MDW–SJC, 09/24/2026: From $389
    24

    Thu

  • MDW–SJC, 09/25/2026: From $304
    25

    Fri

  • MDW–SJC, 09/26/2026: From $304
    26

    Sat

  • MDW–SJC, 09/27/2026: From $314
    27

    Sun

  • MDW–SJC, 09/28/2026: From $304
    28

    Mon

  • MDW–SJC, 09/29/2026: From $304
    29

    Tue

  • MDW–SJC, 09/30/2026: From $304
    30

    Wed

  • MDW–SJC, 10/01/2026: From $304
    01

    Thu

    OCT

  • MDW–SJC, 10/02/2026: From $201
    02

    Fri

  • MDW–SJC, 10/03/2026: From $201
    03

    Sat

  • MDW–SJC, 10/04/2026: From $259
    04

    Sun

  • MDW–SJC, 10/05/2026: From $211
    05

    Mon

  • MDW–SJC, 10/06/2026: From $201
    06

    Tue

  • MDW–SJC, 10/07/2026: From $201
    07

    Wed

  • MDW–SJC, 10/08/2026: From $249
    08

    Thu

  • MDW–SJC, 10/09/2026: From $249
    09

    Fri

  • MDW–SJC, 10/10/2026: From $249
    10

    Sat

  • MDW–SJC, 10/11/2026: From $239
    11

    Sun

    • Range$201-$685

    *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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