Southwest® flights from West Palm Beach to Chicago-Midway from $195

Promo Code

Low fares from West Palm Beach to Chicago-Midway

$

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$195
Seen: 5 hrs ago

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 01/09/2027

One-way

Basic

From
$195
Seen: 9 hrs ago

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$196
Seen: 15 hrs ago

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 01/12/2027

One-way

Basic

From
$196
Seen: 9 hrs ago

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 12/18/2026

One-way

Basic

From
$200
Seen: 1 hour ago

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$210
Seen: 1 hour ago

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Explore flights from West Palm Beach to Chicago-Midway

Nov 2026
From$220*
Seen: 12 hrs ago
One Way/Basic
Dec 2026
From$195*
Seen: 5 hrs ago
One Way/Basic
Jan 2027
From$195*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $195
cmp-daily-histogram-bars-legend-max-price-aria-label $485
Displaying fares for November-2026
  • DJT–MDW, 11/10/2026: From $244
    10

    Tue

    NOV

  • DJT–MDW, 11/11/2026: From $244
    11

    Wed

  • DJT–MDW, 11/12/2026: From $302
    12

    Thu

  • DJT–MDW, 11/13/2026: From $302
    13

    Fri

  • DJT–MDW, 11/14/2026: From $244
    14

    Sat

  • DJT–MDW, 11/15/2026: From $329
    15

    Sun

  • DJT–MDW, 11/16/2026: From $270
    16

    Mon

  • DJT–MDW, 11/17/2026: From $244
    17

    Tue

  • DJT–MDW: cmp-view-offers-disclaimer. Find Offers
    18

    Wed

  • DJT–MDW, 11/19/2026: From $270
    19

    Thu

  • DJT–MDW, 11/20/2026: From $270
    20

    Fri

  • DJT–MDW, 11/21/2026: From $244
    21

    Sat

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

    Sun

  • DJT–MDW, 11/23/2026: From $220
    23

    Mon

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

    Tue

  • DJT–MDW, 11/25/2026: From $220
    25

    Wed

  • DJT–MDW, 11/26/2026: From $220
    26

    Thu

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

    Fri

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

    Sat

  • DJT–MDW, 11/29/2026: From $485
    29

    Sun

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

    Mon

  • DJT–MDW, 12/01/2026: From $221
    01

    Tue

    DEC

  • DJT–MDW, 12/02/2026: From $195
    02

    Wed

  • DJT–MDW, 12/03/2026: From $210
    03

    Thu

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

    Fri

  • DJT–MDW, 12/05/2026: From $210
    05

    Sat

  • DJT–MDW, 12/06/2026: From $225
    06

    Sun

  • DJT–MDW, 12/07/2026: From $270
    07

    Mon

  • DJT–MDW, 12/08/2026: From $210
    08

    Tue

  • DJT–MDW, 12/09/2026: From $196
    09

    Wed

    • Range$195-$485

    *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 Beach International Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    1128 miles

    Questions we hear the most

    There are 101 weekly flights from West Palm Beach to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly West Palm Beach 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 West Palm Beach 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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