Southwest® flights from San Jose, CA to Chicago-Midway from $168

Promo Code

Low fares from San Jose, CA to Chicago-Midway

$

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 11/12/2026

One-way

Basic

From
$168
Seen: 14 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 12/14/2026

One-way

Basic

From
$168
Seen: 15 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 10/20/2026

One-way

Basic

From
$168
Seen: 23 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$168
Seen: 9 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$168
Seen: 9 hrs ago

San Jose, CA (SJC)to

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

One-way

Basic

From
$168
Seen: 7 hrs ago

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Explore flights from San Jose, CA to Chicago-Midway

Sep 2026
From$294*
Seen: 22 hrs ago
One Way/Basic
Oct 2026
From$168*
Seen: 17 hrs ago
One Way/Basic
Nov 2026
From$168*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $168
cmp-daily-histogram-bars-legend-max-price-aria-label $675
Displaying fares for September-2026
  • SJC–MDW, 09/11/2026: From $675
    11

    Fri

    SEP

  • SJC–MDW, 09/12/2026: From $675
    12

    Sat

  • SJC–MDW, 09/13/2026: From $675
    13

    Sun

  • SJC–MDW, 09/14/2026: From $675
    14

    Mon

  • SJC–MDW, 09/15/2026: From $675
    15

    Tue

  • SJC–MDW, 09/16/2026: From $675
    16

    Wed

  • SJC–MDW, 09/17/2026: From $389
    17

    Thu

  • SJC–MDW, 09/18/2026: From $379
    18

    Fri

  • SJC–MDW, 09/19/2026: From $379
    19

    Sat

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

    Sun

  • SJC–MDW, 09/21/2026: From $379
    21

    Mon

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Tue

  • SJC–MDW, 09/23/2026: From $294
    23

    Wed

  • SJC–MDW, 09/24/2026: From $294
    24

    Thu

  • SJC–MDW, 09/25/2026: From $294
    25

    Fri

  • SJC–MDW, 09/26/2026: From $294
    26

    Sat

  • SJC–MDW, 09/27/2026: From $294
    27

    Sun

  • SJC–MDW, 09/28/2026: From $294
    28

    Mon

  • SJC–MDW, 09/29/2026: From $294
    29

    Tue

  • SJC–MDW, 09/30/2026: From $294
    30

    Wed

  • SJC–MDW, 10/01/2026: From $178
    01

    Thu

    OCT

  • SJC–MDW, 10/02/2026: From $195
    02

    Fri

  • SJC–MDW, 10/03/2026: From $168
    03

    Sat

  • SJC–MDW, 10/04/2026: From $239
    04

    Sun

  • SJC–MDW, 10/05/2026: From $168
    05

    Mon

  • SJC–MDW, 10/06/2026: From $168
    06

    Tue

  • SJC–MDW, 10/07/2026: From $168
    07

    Wed

  • SJC–MDW, 10/08/2026: From $217
    08

    Thu

  • SJC–MDW, 10/09/2026: From $195
    09

    Fri

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    10

    Sat

    • Range$168-$675

    *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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