Southwest® flights from Palm Springs to Chicago-Midway from $210

Promo Code

Low fares from Palm Springs to Chicago-Midway

$

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 02/13/2027

One-way

Basic

From
$166
Seen: 20 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 01/19/2027

One-way

Basic

From
$210
Seen: 9 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 11/21/2026

One-way

Basic

From
$214
Seen: 18 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 12/20/2026

One-way

Basic

From
$215
Seen: 19 hrs ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 02/11/2027

One-way

Basic

From
$215
Seen: 38 minutes ago

Palm Springs (PSP)to

Chicago-Midway (MDW)
Depart: 01/29/2027

One-way

Basic

From
$215
Seen: 17 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Palm Springs to Chicago-Midway

Nov 2026
From$214*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$215*
Seen: 19 hrs ago
One Way/Basic
Jan 2027
From$210*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $214
cmp-daily-histogram-bars-legend-max-price-aria-label $459
Displaying fares for November-2026
  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

    NOV

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

    Thu

  • PSP–MDW, 11/13/2026: From $331
    13

    Fri

  • PSP–MDW, 11/14/2026: From $250
    14

    Sat

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

    Sun

  • PSP–MDW, 11/16/2026: From $309
    16

    Mon

  • PSP–MDW, 11/17/2026: From $219
    17

    Tue

  • PSP–MDW, 11/18/2026: From $219
    18

    Wed

  • PSP–MDW, 11/19/2026: From $309
    19

    Thu

  • PSP–MDW, 11/20/2026: From $309
    20

    Fri

  • PSP–MDW, 11/21/2026: From $214
    21

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

  • PSP–MDW, 11/27/2026: From $459
    27

    Fri

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

    Sat

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

    Sun

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

    Mon

  • PSP–MDW, 12/01/2026: From $273
    01

    Tue

    DEC

  • PSP–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • PSP–MDW, 12/03/2026: From $220
    03

    Thu

  • PSP–MDW, 12/04/2026: From $220
    04

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

  • PSP–MDW, 12/10/2026: From $245
    10

    Thu

    • Range$214-$459

    *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

    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.

    Explore Flights from Other Popular Origins

    Popular Flights from Palm Springs