Southwest® flights from San Jose, CA to Chicago-Midway from $191

Promo Code

Low fares from San Jose, CA to Chicago-Midway

$

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 12/30/2026

One-way

Basic

From
$191
Seen: 16 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$191
Seen: 13 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 02/13/2027

One-way

Basic

From
$191
Seen: 9 hrs ago

San Jose, CA (SJC)to

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

One-way

Basic

From
$191
Seen: 7 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 02/09/2027

One-way

Basic

From
$191
Seen: 7 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 02/16/2027

One-way

Basic

From
$191
Seen: 21 hrs ago

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Explore flights from San Jose, CA to Chicago-Midway

Nov 2026
From$319*
Seen: 19 hrs ago
One Way/Basic
Dec 2026
From$191*
Seen: 13 hrs ago
One Way/Basic
Jan 2027
From$191*
Seen: 8 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $191
cmp-daily-histogram-bars-legend-max-price-aria-label $700
Displaying fares for November-2026
  • SJC–MDW, 11/11/2026: From $700
    11

    Wed

    NOV

  • SJC–MDW, 11/12/2026: From $700
    12

    Thu

  • SJC–MDW, 11/13/2026: From $700
    13

    Fri

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

    Sat

  • SJC–MDW, 11/15/2026: From $700
    15

    Sun

  • SJC–MDW, 11/16/2026: From $700
    16

    Mon

  • SJC–MDW, 11/17/2026: From $404
    17

    Tue

  • SJC–MDW, 11/18/2026: From $404
    18

    Wed

  • SJC–MDW, 11/19/2026: From $404
    19

    Thu

  • SJC–MDW, 11/20/2026: From $414
    20

    Fri

  • SJC–MDW, 11/21/2026: From $404
    21

    Sat

  • SJC–MDW, 11/22/2026: From $404
    22

    Sun

  • SJC–MDW, 11/23/2026: From $404
    23

    Mon

  • SJC–MDW, 11/24/2026: From $404
    24

    Tue

  • SJC–MDW, 11/25/2026: From $319
    25

    Wed

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    26

    Thu

  • SJC–MDW, 11/27/2026: From $319
    27

    Fri

  • SJC–MDW, 11/28/2026: From $349
    28

    Sat

  • SJC–MDW, 11/29/2026: From $349
    29

    Sun

  • SJC–MDW, 11/30/2026: From $349
    30

    Mon

  • SJC–MDW, 12/01/2026: From $319
    01

    Tue

    DEC

  • SJC–MDW, 12/02/2026: From $191
    02

    Wed

  • SJC–MDW, 12/03/2026: From $211
    03

    Thu

  • SJC–MDW, 12/04/2026: From $226
    04

    Fri

  • SJC–MDW, 12/05/2026: From $201
    05

    Sat

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

    Sun

  • SJC–MDW, 12/07/2026: From $211
    07

    Mon

  • SJC–MDW, 12/08/2026: From $191
    08

    Tue

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • SJC–MDW, 12/10/2026: From $211
    10

    Thu

    • Range$191-$700

    *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

    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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