Southwest® flights from Des Moines to Chicago (O'Hare)

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Low fares from Des Moines to Chicago (O'Hare)

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Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$119
Seen: 21 hrs ago

Des Moines (DSM)to

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

One-way

Basic

From
$119
Seen: 20 hrs ago

Des Moines (DSM)to

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

One-way

Basic

From
$131
Seen: 23 hrs ago

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 09/19/2026

One-way

Basic

From
$131
Seen: 23 hrs ago

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 10/15/2026

One-way

Basic

From
$131
Seen: 16 hrs ago

Des Moines (DSM)to

Chicago (Midway) (MDW)
Depart: 09/21/2026

One-way

Basic

From
$131
Seen: 15 hrs ago

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Explore flights from Des Moines to Chicago (O'Hare)

Aug 2026
From$131*
Seen: 19 hrs ago
One Way/Basic
Sep 2026
From$119*
Seen: 21 hrs ago
One Way/Basic
Oct 2026
From$131*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $131
cmp-daily-histogram-bars-legend-max-price-aria-label $491
Displaying fares for August-2026
  • DSM–MDW, 08/05/2026: From $323
    05

    Wed

    AUG

  • DSM–MDW, 08/06/2026: From $349
    06

    Thu

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    07

    Fri

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    08

    Sat

  • DSM–MDW, 08/09/2026: From $491
    09

    Sun

  • DSM–MDW, 08/10/2026: From $349
    10

    Mon

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    11

    Tue

  • DSM–MDW, 08/12/2026: From $309
    12

    Wed

  • DSM–MDW, 08/13/2026: From $264
    13

    Thu

  • DSM–MDW, 08/14/2026: From $264
    14

    Fri

  • DSM–MDW, 08/15/2026: From $264
    15

    Sat

  • DSM–MDW, 08/16/2026: From $264
    16

    Sun

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    17

    Mon

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    18

    Tue

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    19

    Wed

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    20

    Thu

  • DSM–MDW, 08/21/2026: From $214
    21

    Fri

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    22

    Sat

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    23

    Sun

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    24

    Mon

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    25

    Tue

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    26

    Wed

  • DSM–MDW, 08/27/2026: From $131
    27

    Thu

  • DSM–MDW, 08/28/2026: From $151
    28

    Fri

  • DSM–MDW, 08/29/2026: From $131
    29

    Sat

  • DSM–MDW, 08/30/2026: From $184
    30

    Sun

  • DSM–MDW, 08/31/2026: From $131
    31

    Mon

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    01

    Tue

    SEP

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    02

    Wed

  • DSM–MDW, 09/03/2026: From $131
    03

    Thu

  • DSM–MDW, 09/04/2026: From $151
    04

    Fri

    • Range$131-$491

    *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:
    O'Hare International Airport
    Distance:
    299 miles

    Route Information

    14† 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 14 weekly flights from Des Moines to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Des Moines to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Des Moines to Chicago (O'Hare)—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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