Southwest® flights from Des Moines to Chicago-Midway from $119

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Low fares from Des Moines to Chicago-Midway

$

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 10/26/2026

One-way

Basic

From
$119
Seen: 9 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 10/24/2026

One-way

Basic

From
$119
Seen: 8 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 10/20/2026

One-way

Basic

From
$119
Seen: 9 hrs ago

Des Moines (DSM)to

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

One-way

Basic

From
$119
Seen: 5 hrs ago

Des Moines (DSM)to

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

One-way

Basic

From
$119
Seen: 16 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 10/27/2026

One-way

Basic

From
$119
Seen: 8 hrs ago

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Explore flights from Des Moines to Chicago-Midway

Sep 2026
From$284*
Seen: 16 hrs ago
One Way/Basic
Oct 2026
From$119*
Seen: 8 hrs ago
One Way/Basic
Nov 2026
From$119*
Seen: 5 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $119
cmp-daily-histogram-bars-legend-max-price-aria-label $294
Displaying fares for September-2026
  • DSM–MDW, 09/30/2026: From $284
    30

    Wed

    SEP

  • DSM–MDW, 10/01/2026: From $284
    01

    Thu

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

    Fri

  • DSM–MDW, 10/03/2026: From $284
    03

    Sat

  • DSM–MDW, 10/04/2026: From $284
    04

    Sun

  • DSM–MDW, 10/05/2026: From $284
    05

    Mon

  • DSM–MDW, 10/06/2026: From $284
    06

    Tue

  • DSM–MDW, 10/07/2026: From $294
    07

    Wed

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

    Thu

  • DSM–MDW, 10/09/2026: From $284
    09

    Fri

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

    Sat

  • DSM–MDW, 10/11/2026: From $284
    11

    Sun

  • DSM–MDW, 10/12/2026: From $284
    12

    Mon

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

    Tue

  • DSM–MDW, 10/14/2026: From $234
    14

    Wed

  • DSM–MDW, 10/15/2026: From $234
    15

    Thu

  • DSM–MDW, 10/16/2026: From $234
    16

    Fri

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

    Sat

  • DSM–MDW, 10/18/2026: From $234
    18

    Sun

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

    Mon

  • DSM–MDW, 10/20/2026: From $119
    20

    Tue

  • DSM–MDW, 10/21/2026: From $119
    21

    Wed

  • DSM–MDW, 10/22/2026: From $165
    22

    Thu

  • DSM–MDW, 10/23/2026: From $149
    23

    Fri

  • DSM–MDW, 10/24/2026: From $119
    24

    Sat

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

    Sun

  • DSM–MDW, 10/26/2026: From $119
    26

    Mon

  • DSM–MDW, 10/27/2026: From $119
    27

    Tue

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

    Wed

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

    Thu

    • Range$119-$294

    *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:
    Des Moines Airport
    Arriving at:
    Chicago Midway International Airport
    Distance:
    306 miles

    Route Information

    46† 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 46 weekly flights from Des Moines to Chicago (Midway) on Southwest Airlines.
    To find the lowest fares by day and time to fly Des Moines 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 Des Moines 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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