Southwest® flights from Palm Springs to Chicago-Midway from $151

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Low fares from Palm Springs to Chicago-Midway

$

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 11/18/2026

One-way

Basic

From
$151
Seen: 4 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 10/21/2026

One-way

Basic

From
$151
Seen: 4 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 11/14/2026

One-way

Basic

From
$156
Seen: 6 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 11/12/2026

One-way

Basic

From
$186
Seen: 7 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 10/01/2026

One-way

Basic

From
$186
Seen: 19 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 11/13/2026

One-way

Basic

From
$190
Seen: 6 hrs ago

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Explore flights from Palm Springs to Chicago-Midway

Sep 2026
From$204*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$151*
Seen: 4 hrs ago
One Way/Basic
Nov 2026
From$151*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $186
cmp-daily-histogram-bars-legend-max-price-aria-label $430
Displaying fares for September-2026
  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

    SEP

  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

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

    Mon

  • PSP–MDW, 09/15/2026: From $204
    15

    Tue

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

    Wed

  • PSP–MDW, 09/17/2026: From $430
    17

    Thu

  • PSP–MDW, 09/18/2026: From $279
    18

    Fri

  • PSP–MDW, 09/19/2026: From $330
    19

    Sat

  • PSP–MDW, 09/20/2026: From $365
    20

    Sun

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

    Mon

  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    22

    Tue

  • PSP–MDW, 09/23/2026: From $300
    23

    Wed

  • PSP–MDW, 09/24/2026: From $260
    24

    Thu

  • PSP–MDW, 09/25/2026: From $269
    25

    Fri

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

    Sat

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

    Sun

  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    28

    Mon

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

    Tue

  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Wed

  • PSP–MDW, 10/01/2026: From $186
    01

    Thu

    OCT

  • PSP–MDW, 10/02/2026: From $190
    02

    Fri

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

    Sat

  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

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

    Mon

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

    Tue

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

    Wed

  • PSP–MDW, 10/08/2026: From $284
    08

    Thu

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

    Fri

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

    Sat

    • Range$186-$430

    *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:
    Palm Springs International Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    1657 miles

    Route Information

    76† Weekly flights

    † 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

    There are 76 weekly flights from Palm Springs to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Palm Springs 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 Palm Springs 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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