Southwest® flights from San Jose, CA to Chicago-Midway from $169

Promo Code

Low fares from San Jose, CA to Chicago-Midway

$

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 12/17/2026

One-way

Basic

From
$169
Seen: 14 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 12/05/2026

One-way

Basic

From
$169
Seen: 14 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 11/03/2026

One-way

Basic

From
$169
Seen: 9 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$169
Seen: 10 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 10/29/2026

One-way

Basic

From
$169
Seen: 10 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 11/10/2026

One-way

Basic

From
$169
Seen: 16 hrs ago

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Explore flights from San Jose, CA to Chicago-Midway

Oct 2026
From$169*
Seen: 10 hrs ago
One Way/Basic
Nov 2026
From$169*
Seen: 7 hrs ago
One Way/Basic
Dec 2026
From$169*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $169
cmp-daily-histogram-bars-legend-max-price-aria-label $685
Displaying fares for October-2026
  • SJC–MDW, 10/01/2026: From $685
    01

    Thu

    OCT

  • SJC–MDW, 10/02/2026: From $685
    02

    Fri

  • SJC–MDW, 10/03/2026: From $685
    03

    Sat

  • SJC–MDW, 10/04/2026: From $685
    04

    Sun

  • SJC–MDW, 10/05/2026: From $685
    05

    Mon

  • SJC–MDW, 10/06/2026: From $389
    06

    Tue

  • SJC–MDW, 10/07/2026: From $389
    07

    Wed

  • SJC–MDW, 10/08/2026: From $389
    08

    Thu

  • SJC–MDW, 10/09/2026: From $389
    09

    Fri

  • SJC–MDW, 10/10/2026: From $389
    10

    Sat

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Sun

  • SJC–MDW, 10/12/2026: From $389
    12

    Mon

  • SJC–MDW, 10/13/2026: From $304
    13

    Tue

  • SJC–MDW, 10/14/2026: From $304
    14

    Wed

  • SJC–MDW, 10/15/2026: From $309
    15

    Thu

  • SJC–MDW, 10/16/2026: From $304
    16

    Fri

  • SJC–MDW, 10/17/2026: From $304
    17

    Sat

  • SJC–MDW, 10/18/2026: From $304
    18

    Sun

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Mon

  • SJC–MDW, 10/20/2026: From $304
    20

    Tue

  • SJC–MDW, 10/21/2026: From $169
    21

    Wed

  • SJC–MDW, 10/22/2026: From $169
    22

    Thu

  • SJC–MDW, 10/23/2026: From $205
    23

    Fri

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

    Sat

  • SJC–MDW, 10/25/2026: From $249
    25

    Sun

  • SJC–MDW, 10/26/2026: From $169
    26

    Mon

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Tue

  • SJC–MDW, 10/28/2026: From $169
    28

    Wed

  • SJC–MDW, 10/29/2026: From $169
    29

    Thu

  • SJC–MDW, 10/30/2026: From $205
    30

    Fri

  • SJC–MDW, 10/31/2026: From $169
    31

    Sat

    • Range$169-$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:
    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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