Southwest® flights from Des Moines to Chicago (Midway) from $131

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Low fares from Des Moines to Chicago (Midway)

$

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 10/01/2026

One-way

Basic

From
$131
Seen: 22 hrs ago

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 11/03/2026

One-way

Basic

From
$131
Seen: 10 hrs ago

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 11/19/2026

One-way

Basic

From
$131
Seen: 14 hrs ago

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 09/15/2026

One-way

Basic

From
$131
Seen: 3 hrs ago

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$131
Seen: 3 hrs ago

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 11/18/2026

One-way

Basic

From
$131
Seen: 15 hrs ago

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Explore flights from Des Moines to Chicago (Midway)

Aug 2026
From$264*
Seen: 20 hrs ago
One Way/Basic
Sep 2026
From$131*
Seen: 15 hrs ago
One Way/Basic
Oct 2026
From$131*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $131
cmp-daily-histogram-bars-legend-max-price-aria-label $264
Displaying fares for August-2026
  • DSM–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Fri

    AUG

  • DSM–MDW, 08/22/2026: From $264
    22

    Sat

  • DSM–MDW, 08/23/2026: From $264
    23

    Sun

  • DSM–MDW, 08/24/2026: From $264
    24

    Mon

  • DSM–MDW, 08/25/2026: From $264
    25

    Tue

  • DSM–MDW, 08/26/2026: From $264
    26

    Wed

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

    Thu

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

    Fri

  • DSM–MDW, 08/29/2026: From $264
    29

    Sat

  • DSM–MDW, 08/30/2026: From $264
    30

    Sun

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

    Mon

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

    Tue

    SEP

  • DSM–MDW, 09/02/2026: From $264
    02

    Wed

  • DSM–MDW, 09/03/2026: From $214
    03

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

  • DSM–MDW, 09/08/2026: From $214
    08

    Tue

  • DSM–MDW, 09/09/2026: From $214
    09

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

  • DSM–MDW, 09/15/2026: From $131
    15

    Tue

  • DSM–MDW, 09/16/2026: From $131
    16

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

    • Range$131-$264

    *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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