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

Promo Code

Low fares from Chicago-Midway to West Palm Beach

$

Chicago-Midway (MDW)to

West Palm Beach (DJT)
Depart: 01/08/2027

One-way

Basic

From
$149
Seen: 2 hrs ago

Chicago-Midway (MDW)to

West Palm Beach (DJT)
Depart: 12/11/2026

One-way

Basic

From
$149
Seen: 2 hrs ago

Chicago-Midway (MDW)to

West Palm Beach (DJT)
Depart: 11/10/2026

One-way

Basic

From
$149
Seen: 51 minutes ago

Chicago-Midway (MDW)to

West Palm Beach (DJT)
Depart: 12/12/2026

One-way

Basic

From
$180
Seen: 16 hrs ago

Chicago-Midway (MDW)to

West Palm Beach (DJT)
Depart: 11/13/2026

One-way

Basic

From
$180
Seen: 7 hrs ago

Chicago-Midway (MDW)to

West Palm Beach (DJT)
Depart: 10/28/2026

One-way

Basic

From
$180
Seen: 11 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 Chicago-Midway to West Palm Beach

Oct 2026
From$180*
Seen: 12 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 51 minutes 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 $287
Displaying fares for October-2026
  • MDW–DJT, 10/02/2026: From $287
    02

    Fri

    OCT

  • MDW–DJT, 10/03/2026: From $229
    03

    Sat

  • MDW–DJT: cmp-view-offers-disclaimer. Find Offers
    04

    Sun

  • MDW–DJT, 10/05/2026: From $287
    05

    Mon

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

    Tue

  • MDW–DJT, 10/07/2026: From $234
    07

    Wed

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

    Thu

  • MDW–DJT, 10/09/2026: From $260
    09

    Fri

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

    Sat

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

    Sun

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

    Mon

  • MDW–DJT, 10/13/2026: From $234
    13

    Tue

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

    Wed

  • MDW–DJT, 10/15/2026: From $255
    15

    Thu

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

    Fri

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

    Sat

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

    Sun

  • MDW–DJT, 10/19/2026: From $205
    19

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

  • MDW–DJT, 10/24/2026: From $205
    24

    Sat

  • MDW–DJT, 10/25/2026: From $214
    25

    Sun

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

    Mon

  • MDW–DJT, 10/27/2026: From $180
    27

    Tue

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

    Wed

  • MDW–DJT, 10/29/2026: From $185
    29

    Thu

  • MDW–DJT, 10/30/2026: From $185
    30

    Fri

  • MDW–DJT, 10/31/2026: From $180
    31

    Sat

  • MDW–DJT, 11/01/2026: From $205
    01

    Sun

    NOV

    • Range$180-$287

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

    Route Information

    92† 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 92 weekly flights from Chicago (Midway) to West Palm Beach on Southwest Airlines.
    To find the lowest fares by day and time to fly Chicago (Midway) to West Palm Beach with Southwest, check out our Low Fare Calendar.
    You can rent a car at Palm Beach International Airport book yours with your flight.
    Yes! Flights from Chicago (Midway) to West Palm Beach—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 Chicago-Midway