Southwest® flights from Des Moines to Chicago-Midway from $114

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Low fares from Des Moines to Chicago-Midway

$

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 11/21/2026

One-way

Basic

From
$114
Seen: 20 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 12/18/2026

One-way

Basic

From
$114
Seen: 20 minutes ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 11/13/2026

One-way

Basic

From
$114
Seen: 19 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 12/21/2026

One-way

Basic

From
$114
Seen: 15 hrs ago

Des Moines (DSM)to

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

One-way

Basic

From
$114
Seen: 19 hrs ago

Des Moines (DSM)to

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

One-way

Basic

From
$114
Seen: 22 hrs ago

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Explore flights from Des Moines to Chicago-Midway

Oct 2026
From$249*
Seen: 4 hrs ago
One Way/Basic
Nov 2026
From$114*
Seen: 19 hrs ago
One Way/Basic
Dec 2026
From$114*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $114
cmp-daily-histogram-bars-legend-max-price-aria-label $294
Displaying fares for October-2026
  • DSM–MDW: cmp-view-offers-disclaimer. Find Offers
    21

    Wed

    OCT

  • DSM–MDW, 10/22/2026: From $294
    22

    Thu

  • DSM–MDW, 10/23/2026: From $294
    23

    Fri

  • DSM–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

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

    Sun

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

    Mon

  • DSM–MDW, 10/27/2026: From $294
    27

    Tue

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

    Wed

  • DSM–MDW, 10/29/2026: From $294
    29

    Thu

  • DSM–MDW, 10/30/2026: From $249
    30

    Fri

  • DSM–MDW, 10/31/2026: From $294
    31

    Sat

  • DSM–MDW, 11/01/2026: From $294
    01

    Sun

    NOV

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

    Mon

  • DSM–MDW, 11/03/2026: From $244
    03

    Tue

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

    Wed

  • DSM–MDW, 11/05/2026: From $244
    05

    Thu

  • DSM–MDW, 11/06/2026: From $244
    06

    Fri

  • DSM–MDW, 11/07/2026: From $244
    07

    Sat

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

    Sun

  • DSM–MDW, 11/09/2026: From $114
    09

    Mon

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

    Tue

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

    Wed

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

    Thu

  • DSM–MDW, 11/13/2026: From $114
    13

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

  • DSM–MDW, 11/19/2026: From $114
    19

    Thu

  • DSM–MDW, 11/20/2026: From $163
    20

    Fri

    • Range$114-$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

    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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