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

Promo Code

Low fares from Chicago-Midway to San Jose, CA

$

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 01/20/2027

One-way

Basic

From
$150
Seen: 20 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 01/21/2027

One-way

Basic

From
$150
Seen: 4 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 12/07/2026

One-way

Basic

From
$150
Seen: 8 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 12/14/2026

One-way

Basic

From
$150
Seen: 4 hrs ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 12/21/2026

One-way

Basic

From
$150
Seen: 57 minutes ago

Chicago-Midway (MDW)to

San Jose, CA (SJC)
Depart: 12/10/2026

One-way

Basic

From
$150
Seen: 19 hrs ago

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Explore flights from Chicago-Midway to San Jose, CA

Oct 2026
From$399*
Seen: 18 hrs ago
One Way/Basic
Nov 2026
From$150*
Seen: 1 hour ago
One Way/Basic
Dec 2026
From$150*
Seen: 3 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
  • MDW–SJC, 10/23/2026: From $695
    23

    Fri

    OCT

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

    Sat

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

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

    Mon

  • MDW–SJC, 10/27/2026: From $695
    27

    Tue

  • MDW–SJC, 10/28/2026: From $695
    28

    Wed

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    29

    Thu

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

    Fri

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

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

    Sun

    NOV

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

    Mon

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

    Tue

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

    Wed

  • MDW–SJC, 11/05/2026: From $314
    05

    Thu

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

    Fri

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

    Sat

  • MDW–SJC, 11/08/2026: From $319
    08

    Sun

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

    Mon

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

    Tue

  • MDW–SJC, 11/11/2026: From $182
    11

    Wed

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

    Thu

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

    Fri

  • MDW–SJC, 11/14/2026: From $259
    14

    Sat

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

    Sun

  • MDW–SJC: cmp-view-offers-disclaimer. Find Offers
    16

    Mon

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

    Tue

  • MDW–SJC, 11/18/2026: From $162
    18

    Wed

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

    Thu

  • MDW–SJC, 11/20/2026: From $220
    20

    Fri

  • MDW–SJC, 11/21/2026: From $249
    21

    Sat

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