Southwest® flights from Des Moines to Chicago-Midway from $130

Promo Code

Low fares from Des Moines to Chicago-Midway

$

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$130
Seen: 19 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 12/16/2026

One-way

Basic

From
$130
Seen: 19 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 01/12/2027

One-way

Basic

From
$130
Seen: 21 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 01/16/2027

One-way

Basic

From
$135
Seen: 1 hour ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 01/11/2027

One-way

Basic

From
$145
Seen: 20 hrs ago

Des Moines (DSM)to

Chicago-Midway (MDW)
Depart: 12/03/2026

One-way

Basic

From
$145
Seen: 21 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 Des Moines to Chicago-Midway

Nov 2026
From$249*
Seen: 14 hrs ago
One Way/Basic
Dec 2026
From$130*
Seen: 19 hrs ago
One Way/Basic
Jan 2027
From$130*
Seen: 21 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $145
cmp-daily-histogram-bars-legend-max-price-aria-label $299
Displaying fares for November-2026
  • DSM–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

    NOV

  • DSM–MDW, 11/12/2026: From $299
    12

    Thu

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

    Fri

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

    Sat

  • DSM–MDW, 11/15/2026: From $299
    15

    Sun

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

    Mon

  • DSM–MDW, 11/17/2026: From $299
    17

    Tue

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

    Wed

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

    Thu

  • DSM–MDW, 11/20/2026: From $299
    20

    Fri

  • DSM–MDW, 11/21/2026: From $299
    21

    Sat

  • DSM–MDW, 11/22/2026: From $299
    22

    Sun

  • DSM–MDW, 11/23/2026: From $299
    23

    Mon

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

    Tue

  • DSM–MDW, 11/25/2026: From $249
    25

    Wed

  • DSM–MDW, 11/26/2026: From $249
    26

    Thu

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

    Fri

  • DSM–MDW, 11/28/2026: From $279
    28

    Sat

  • DSM–MDW, 11/29/2026: From $279
    29

    Sun

  • DSM–MDW, 11/30/2026: From $279
    30

    Mon

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

    Tue

    DEC

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

    Wed

  • DSM–MDW, 12/03/2026: From $145
    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: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • DSM–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

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

    Thu

    • Range$145-$299

    *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.

    Explore Flights from Other Popular Origins

    Popular Flights from Des Moines