Southwest® flights from West Palm Beach to Chicago (Midway) from $160

Promo Code

Low fares from West Palm Beach to Chicago (Midway)

$

West Palm Beach (DJT)to

Chicago (Midway) (MDW)
Depart: 09/23/2026

One-way

Basic

From
$160
Seen: 15 hrs ago

West Palm Beach (DJT)to

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

One-way

Basic

From
$160
Seen: 20 hrs ago

West Palm Beach (DJT)to

Chicago (Midway) (MDW)
Depart: 10/23/2026

One-way

Basic

From
$160
Seen: 18 hrs ago

West Palm Beach (DJT)to

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

One-way

Basic

From
$160
Seen: 7 hrs ago

West Palm Beach (DJT)to

Chicago (Midway) (MDW)
Depart: 11/05/2026

One-way

Basic

From
$160
Seen: 5 hrs ago

West Palm Beach (DJT)to

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

One-way

Basic

From
$160
Seen: 3 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 West Palm Beach to Chicago (Midway)

Aug 2026
From$172*
Seen: 6 hrs ago
One Way/Basic
Sep 2026
From$160*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$160*
Seen: 1 hour ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $160
cmp-daily-histogram-bars-legend-max-price-aria-label $267
Displaying fares for August-2026
  • DJT–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

    AUG

  • DJT–MDW, 08/22/2026: From $209
    22

    Sat

  • DJT–MDW, 08/23/2026: From $267
    23

    Sun

  • DJT–MDW, 08/24/2026: From $218
    24

    Mon

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

    Tue

  • DJT–MDW, 08/26/2026: From $209
    26

    Wed

  • DJT–MDW, 08/27/2026: From $218
    27

    Thu

  • DJT–MDW, 08/28/2026: From $218
    28

    Fri

  • DJT–MDW, 08/29/2026: From $172
    29

    Sat

  • DJT–MDW, 08/30/2026: From $235
    30

    Sun

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

    Mon

  • DJT–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • DJT–MDW, 09/02/2026: From $172
    02

    Wed

  • DJT–MDW, 09/03/2026: From $218
    03

    Thu

  • DJT–MDW, 09/04/2026: From $185
    04

    Fri

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

    Sat

  • DJT–MDW, 09/06/2026: From $235
    06

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

  • DJT–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

  • DJT–MDW, 09/17/2026: From $160
    17

    Thu

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

    Fri

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

    Sat

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

    Sun

    • Range$160-$267

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from West Palm Beach