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

Promo Code

Low fares from Chicago-Midway to San Jose, CA

$

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 02/16/2027

One-way

Basic

From
$191
Seen: 23 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 12/16/2026

One-way

Basic

From
$191
Seen: 2 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 02/06/2027

One-way

Basic

From
$191
Seen: 14 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 12/08/2026

One-way

Basic

From
$191
Seen: 10 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 01/09/2027

One-way

Basic

From
$191
Seen: 19 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 01/13/2027

One-way

Basic

From
$191
Seen: 4 hrs ago

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Explore flights from Chicago-Midway to San Jose, CA

Nov 2026
From$319*
Seen: 1 hour ago
One Way/Basic
Dec 2026
From$191*
Seen: 10 hrs ago
One Way/Basic
Jan 2027
From$191*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $191
cmp-daily-histogram-bars-legend-max-price-aria-label $705
Displaying fares for November-2026
  • MDW–SJC, 11/13/2026: From $705
    13

    Fri

    NOV

  • MDW–SJC, 11/14/2026: From $705
    14

    Sat

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • MDW–SJC, 11/16/2026: From $705
    16

    Mon

  • MDW–SJC, 11/17/2026: From $700
    17

    Tue

  • MDW–SJC, 11/18/2026: From $700
    18

    Wed

  • MDW–SJC, 11/19/2026: From $705
    19

    Thu

  • MDW–SJC, 11/20/2026: From $404
    20

    Fri

  • MDW–SJC, 11/21/2026: From $409
    21

    Sat

  • MDW–SJC, 11/22/2026: From $409
    22

    Sun

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    23

    Mon

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

    Tue

  • MDW–SJC, 11/25/2026: From $404
    25

    Wed

  • MDW–SJC, 11/26/2026: From $319
    26

    Thu

  • MDW–SJC, 11/27/2026: From $329
    27

    Fri

  • MDW–SJC, 11/28/2026: From $444
    28

    Sat

  • MDW–SJC, 11/29/2026: From $510
    29

    Sun

  • MDW–SJC, 11/30/2026: From $364
    30

    Mon

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

    Tue

    DEC

  • MDW–SJC, 12/02/2026: From $319
    02

    Wed

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

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

    Fri

  • MDW–SJC, 12/05/2026: From $211
    05

    Sat

  • MDW–SJC, 12/06/2026: From $269
    06

    Sun

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    07

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

  • MDW–SJC, 12/12/2026: From $216
    12

    Sat

    • Range$191-$705

    *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

    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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