Southwest® flights from San Jose, CA to Chicago-Midway from $150

Promo Code

Low fares from San Jose, CA to Chicago-Midway

$

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 01/20/2027

One-way

Basic

From
$150
Seen: 11 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 01/11/2027

One-way

Basic

From
$150
Seen: 13 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 01/04/2027

One-way

Basic

From
$150
Seen: 10 hrs ago

San Jose, CA (SJC)to

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

One-way

Basic

From
$150
Seen: 6 hrs ago

San Jose, CA (SJC)to

Chicago-Midway (MDW)
Depart: 01/18/2027

One-way

Basic

From
$150
Seen: 39 minutes ago

San Jose, CA (SJC)to

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

One-way

Basic

From
$150
Seen: 12 hrs ago

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Explore flights from San Jose, CA to Chicago-Midway

Oct 2026
From$399*
Seen: 6 hrs ago
One Way/Basic
Nov 2026
From$150*
Seen: 4 hrs ago
One Way/Basic
Dec 2026
From$150*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $162
cmp-daily-histogram-bars-legend-max-price-aria-label $695
Displaying fares for October-2026
  • SJC–MDW, 10/23/2026: From $695
    23

    Fri

    OCT

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

    Sat

  • SJC–MDW, 10/25/2026: From $695
    25

    Sun

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

    Mon

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

    Tue

  • SJC–MDW, 10/28/2026: From $399
    28

    Wed

  • SJC–MDW, 10/29/2026: From $399
    29

    Thu

  • SJC–MDW, 10/30/2026: From $399
    30

    Fri

  • SJC–MDW, 10/31/2026: From $399
    31

    Sat

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Sun

    NOV

  • SJC–MDW, 11/02/2026: From $399
    02

    Mon

  • SJC–MDW, 11/03/2026: From $399
    03

    Tue

  • SJC–MDW, 11/04/2026: From $314
    04

    Wed

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Thu

  • SJC–MDW, 11/06/2026: From $314
    06

    Fri

  • SJC–MDW, 11/07/2026: From $314
    07

    Sat

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Sun

  • SJC–MDW, 11/09/2026: From $167
    09

    Mon

  • SJC–MDW, 11/10/2026: From $167
    10

    Tue

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

    Wed

  • SJC–MDW, 11/12/2026: From $162
    12

    Thu

  • SJC–MDW, 11/13/2026: From $167
    13

    Fri

  • SJC–MDW, 11/14/2026: From $269
    14

    Sat

  • SJC–MDW, 11/15/2026: From $167
    15

    Sun

  • SJC–MDW, 11/16/2026: From $162
    16

    Mon

  • SJC–MDW, 11/17/2026: From $162
    17

    Tue

  • SJC–MDW, 11/18/2026: From $171
    18

    Wed

  • SJC–MDW, 11/19/2026: From $269
    19

    Thu

  • SJC–MDW, 11/20/2026: From $282
    20

    Fri

  • SJC–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Sat

  • SJC–MDW, 11/22/2026: From $167
    22

    Sun

    • Range$162-$695

    *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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