Southwest® flights from Palm Springs to Chicago (O'Hare)

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Low fares from Palm Springs to Chicago (O'Hare)

$

Palm Springs (PSP)to

Chicago (Midway) (MDW)
Depart: 09/11/2026

One-way

Basic

From
$141
Seen: 14 hrs ago

Palm Springs (PSP)to

Chicago (Midway) (MDW)
Depart: 11/04/2026

One-way

Basic

From
$141
Seen: 7 hrs ago

Palm Springs (PSP)to

Chicago (Midway) (MDW)
Depart: 10/02/2026

One-way

Basic

From
$180
Seen: 20 hrs ago

Palm Springs (PSP)to

Chicago (Midway) (MDW)
Depart: 09/22/2026

One-way

Basic

From
$184
Seen: 19 hrs ago

Palm Springs (PSP)to

Chicago (Midway) (MDW)
Depart: 09/01/2026

One-way

Basic

From
$184
Seen: 14 hrs ago

Palm Springs (PSP)to

Chicago (Midway) (MDW)
Depart: 12/01/2026

One-way

Basic

From
$185
Seen: 3 hrs ago

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Explore flights from Palm Springs to Chicago (O'Hare)

Aug 2026
From$204*
Seen: 19 hrs ago
One Way/Basic
Sep 2026
From$141*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$180*
Seen: 20 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $141
cmp-daily-histogram-bars-legend-max-price-aria-label $355
Displaying fares for August-2026
  • PSP–MDW, 08/26/2026: From $230
    26

    Wed

    AUG

  • PSP–MDW, 08/27/2026: From $269
    27

    Thu

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

    Fri

  • PSP–MDW, 08/29/2026: From $204
    29

    Sat

  • PSP–MDW, 08/30/2026: From $350
    30

    Sun

  • PSP–MDW, 08/31/2026: From $269
    31

    Mon

  • PSP–MDW, 09/01/2026: From $184
    01

    Tue

    SEP

  • PSP–MDW, 09/02/2026: From $199
    02

    Wed

  • PSP–MDW, 09/03/2026: From $320
    03

    Thu

  • PSP–MDW, 09/04/2026: From $269
    04

    Fri

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

    Sat

  • PSP–MDW, 09/06/2026: From $297
    06

    Sun

  • PSP–MDW, 09/07/2026: From $355
    07

    Mon

  • PSP–MDW, 09/08/2026: From $274
    08

    Tue

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

    Wed

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

    Thu

  • PSP–MDW, 09/11/2026: From $141
    11

    Fri

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

    Sat

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

    Sun

  • PSP–MDW, 09/14/2026: From $255
    14

    Mon

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

    Tue

  • PSP–MDW, 09/16/2026: From $258
    16

    Wed

  • PSP–MDW, 09/17/2026: From $264
    17

    Thu

  • PSP–MDW, 09/18/2026: From $235
    18

    Fri

  • PSP–MDW, 09/19/2026: From $253
    19

    Sat

  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

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

    Mon

  • PSP–MDW, 09/22/2026: From $184
    22

    Tue

  • PSP–MDW, 09/23/2026: From $258
    23

    Wed

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

    Thu

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

    Fri

    • Range$141-$355

    *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:
    O'Hare International Airport
    Distance:
    1651 miles

    Route Information

    47† 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 47 weekly flights from Palm Springs to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Palm Springs to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Palm Springs to Chicago (O'Hare)—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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