Southwest® flights from West Palm Beach to Chicago-Midway from $149

Promo Code

Low fares from West Palm Beach to Chicago-Midway

$

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 12/14/2026

One-way

Basic

From
$149
Seen: 2 hrs ago

West Palm Beach (DJT)to

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

One-way

Basic

From
$180
Seen: 13 hrs ago

West Palm Beach (DJT)to

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

One-way

Basic

From
$180
Seen: 19 hrs ago

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 10/29/2026

One-way

Basic

From
$180
Seen: 10 hrs ago

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 10/28/2026

One-way

Basic

From
$180
Seen: 17 hrs ago

West Palm Beach (DJT)to

Chicago-Midway (MDW)
Depart: 12/24/2026

One-way

Basic

From
$180
Seen: 15 hrs ago

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Explore flights from West Palm Beach to Chicago-Midway

Oct 2026
From$180*
Seen: 10 hrs ago
One Way/Basic
Nov 2026
From$180*
Seen: 12 hrs ago
One Way/Basic
Dec 2026
From$149*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $180
cmp-daily-histogram-bars-legend-max-price-aria-label $337
Displaying fares for October-2026
  • DJT–MDW, 10/02/2026: From $287
    02

    Fri

    OCT

  • DJT–MDW, 10/03/2026: From $234
    03

    Sat

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    04

    Sun

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    05

    Mon

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    06

    Tue

  • DJT–MDW, 10/07/2026: From $229
    07

    Wed

  • DJT–MDW, 10/08/2026: From $255
    08

    Thu

  • DJT–MDW, 10/09/2026: From $255
    09

    Fri

  • DJT–MDW, 10/10/2026: From $229
    10

    Sat

  • DJT–MDW, 10/11/2026: From $255
    11

    Sun

  • DJT–MDW, 10/12/2026: From $260
    12

    Mon

  • DJT–MDW, 10/13/2026: From $229
    13

    Tue

  • DJT–MDW, 10/14/2026: From $229
    14

    Wed

  • DJT–MDW, 10/15/2026: From $205
    15

    Thu

  • DJT–MDW, 10/16/2026: From $205
    16

    Fri

  • DJT–MDW: cmp-view-offers-disclaimer. Find Offers
    17

    Sat

  • DJT–MDW, 10/18/2026: From $319
    18

    Sun

  • DJT–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Mon

  • DJT–MDW, 10/20/2026: From $205
    20

    Tue

  • DJT–MDW, 10/21/2026: From $205
    21

    Wed

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    22

    Thu

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

    Fri

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    24

    Sat

  • DJT–MDW, 10/25/2026: From $337
    25

    Sun

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    26

    Mon

  • DJT–MDW, 10/27/2026: From $185
    27

    Tue

  • DJT–MDW, 10/28/2026: From $180
    28

    Wed

  • DJT–MDW, 10/29/2026: From $180
    29

    Thu

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    30

    Fri

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

    Sat

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    01

    Sun

    NOV

    • Range$180-$337

    *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

    Route Information

    101† 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 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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