All airlines flying from Des Moines (DSM) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Direct Flights:
Sat 12:10 Des Moines (DSM) 13:30 Chicago Midway (MDW) Southwest Airlines WN 295 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-08-08 through 2026-09-26
Sun 15:50 Des Moines (DSM) 17:10 Chicago Midway (MDW) Southwest Airlines WN 295 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 15:50 Des Moines (DSM) 17:10 Chicago Midway (MDW) Southwest Airlines WN 424 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-08-06 through 2026-09-28
Sun 15:55 Des Moines (DSM) 17:15 Chicago Midway (MDW) Southwest Airlines WN 698 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Operates only on 2026-05-24
Sat 15:35 Des Moines (DSM) 17:00 Chicago Midway (MDW) Southwest Airlines WN 1524 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-06-06 through 2026-08-01
Tue,Wed 15:45 Des Moines (DSM) 17:05 Chicago Midway (MDW) Southwest Airlines WN 1524 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-06-09 through 2026-07-29
Sun 16:15 Des Moines (DSM) 17:35 Chicago Midway (MDW) Southwest Airlines WN 1524 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-06-07 through 2026-08-02
Sat 05:25 Des Moines (DSM) 06:40 Chicago Midway (MDW) Southwest Airlines WN 1715 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-08-08 through 2026-09-26
Sun 05:40 Des Moines (DSM) 07:00 Chicago Midway (MDW) Southwest Airlines WN 1715 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-08-09 through 2026-09-27
Tue,Wed 06:15 Des Moines (DSM) 07:35 Chicago Midway (MDW) Southwest Airlines WN 1715 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 05:40 Des Moines (DSM) 07:00 Chicago Midway (MDW) Southwest Airlines WN 1727 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-08-06 through 2026-09-28
Mon,Thu,Fri 16:40 Des Moines (DSM) 18:00 Chicago Midway (MDW) Southwest Airlines WN 1755 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 05:10 Des Moines (DSM) 06:30 Chicago Midway (MDW) Southwest Airlines WN 1772 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-06-04 through 2026-08-03
Sat,Sun 05:10 Des Moines (DSM) 06:30 Chicago Midway (MDW) Southwest Airlines WN 1772 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-06-06 through 2026-08-02
Tue,Wed 05:20 Des Moines (DSM) 06:40 Chicago Midway (MDW) Southwest Airlines WN 1772 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-06-09 through 2026-07-29
Sun 05:20 Des Moines (DSM) 06:40 Chicago Midway (MDW) Southwest Airlines WN 2128 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-04-12 through 2026-05-17
Sun 05:20 Des Moines (DSM) 06:40 Chicago Midway (MDW) Southwest Airlines WN 2128 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Operates only on 2026-05-31
Mon,Thu,Fri 05:25 Des Moines (DSM) 06:45 Chicago Midway (MDW) Southwest Airlines WN 2128 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-04-09 through 2026-06-01
Tue,Wed 05:30 Des Moines (DSM) 06:55 Chicago Midway (MDW) Southwest Airlines WN 2128 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-04-07 through 2026-06-03
Sat 05:35 Des Moines (DSM) 06:55 Chicago Midway (MDW) Southwest Airlines WN 2128 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-04-11 through 2026-05-30
Sun 06:00 Des Moines (DSM) 07:20 Chicago Midway (MDW) Southwest Airlines WN 2128 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Operates only on 2026-05-24
Tue,Wed 15:15 Des Moines (DSM) 16:35 Chicago Midway (MDW) Southwest Airlines WN 2131 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 16:20 Des Moines (DSM) 17:40 Chicago Midway (MDW) Southwest Airlines WN 2131 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-04-09 through 2026-06-01
Sun 16:20 Des Moines (DSM) 17:40 Chicago Midway (MDW) Southwest Airlines WN 2131 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-04-12 through 2026-05-17
Sun 16:20 Des Moines (DSM) 17:40 Chicago Midway (MDW) Southwest Airlines WN 2131 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Operates only on 2026-05-31
Sat 05:20 Des Moines (DSM) 06:40 Chicago Midway (MDW) Southwest Airlines WN 2845 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-07 through 2026-04-04
Sun 05:25 Des Moines (DSM) 06:45 Chicago Midway (MDW) Southwest Airlines WN 2845 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-08 through 2026-04-05
Tue,Wed 05:30 Des Moines (DSM) 06:50 Chicago Midway (MDW) Southwest Airlines WN 2845 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 05:35 Des Moines (DSM) 06:55 Chicago Midway (MDW) Southwest Airlines WN 2845 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-05 through 2026-04-06
Tue,Wed 15:40 Des Moines (DSM) 16:55 Chicago Midway (MDW) Southwest Airlines WN 2849 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 16:20 Des Moines (DSM) 17:40 Chicago Midway (MDW) Southwest Airlines WN 2849 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-03-05 through 2026-04-06
Sat 16:35 Des Moines (DSM) 17:55 Chicago Midway (MDW) Southwest Airlines WN 2849 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-03-07 through 2026-04-04
Sun 16:40 Des Moines (DSM) 18:00 Chicago Midway (MDW) Southwest Airlines WN 2849 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-03-08 through 2026-04-05
Tue 14:40 Des Moines (DSM) 16:00 Chicago Midway (MDW) Southwest Airlines WN 5088 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-08-04 through 2026-09-29
Wed 14:40 Des Moines (DSM) 16:00 Chicago Midway (MDW) Southwest Airlines WN 5101 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-08-05 through 2026-09-30

A domestic route departing from the Des Moines airport (DSM) and arriving at Chicago Midway airport (MDW).
The flight distance is 305 miles, or 491 km.
The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
For direct flights, the flight time varies between 1:15 and 1:25.

Return (MDW-DSM) flights

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All airlines flying from Des Moines (DSM) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN295

12:10

Des Moines (DSM)

13:30

Chicago Midway (MDW)

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN295

15:50

Des Moines (DSM)

17:10

Chicago Midway (MDW)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN424

15:50

Des Moines (DSM)

17:10

Chicago Midway (MDW)

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN698

15:55

Des Moines (DSM)

17:15

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1524

15:35

Des Moines (DSM)

17:00

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1524

15:45

Des Moines (DSM)

17:05

Chicago Midway (MDW)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1524

16:15

Des Moines (DSM)

17:35

Chicago Midway (MDW)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1715

05:25

Des Moines (DSM)

06:40

Chicago Midway (MDW)

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1715

05:40

Des Moines (DSM)

07:00

Chicago Midway (MDW)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1715

06:15

Des Moines (DSM)

07:35

Chicago Midway (MDW)

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1727

05:40

Des Moines (DSM)

07:00

Chicago Midway (MDW)

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1755

16:40

Des Moines (DSM)

18:00

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1772

05:10

Des Moines (DSM)

06:30

Chicago Midway (MDW)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1772

05:10

Des Moines (DSM)

06:30

Chicago Midway (MDW)

Effective 2026-06-06 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1772

05:20

Des Moines (DSM)

06:40

Chicago Midway (MDW)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2128

05:20

Des Moines (DSM)

06:40

Chicago Midway (MDW)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2128

05:20

Des Moines (DSM)

06:40

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2128

05:25

Des Moines (DSM)

06:45

Chicago Midway (MDW)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2128

05:30

Des Moines (DSM)

06:55

Chicago Midway (MDW)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2128

05:35

Des Moines (DSM)

06:55

Chicago Midway (MDW)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2128

06:00

Des Moines (DSM)

07:20

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2131

15:15

Des Moines (DSM)

16:35

Chicago Midway (MDW)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2131

16:20

Des Moines (DSM)

17:40

Chicago Midway (MDW)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2131

16:20

Des Moines (DSM)

17:40

Chicago Midway (MDW)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2131

16:20

Des Moines (DSM)

17:40

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2845

05:20

Des Moines (DSM)

06:40

Chicago Midway (MDW)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2845

05:25

Des Moines (DSM)

06:45

Chicago Midway (MDW)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2845

05:30

Des Moines (DSM)

06:50

Chicago Midway (MDW)

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2845

05:35

Des Moines (DSM)

06:55

Chicago Midway (MDW)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2849

15:40

Des Moines (DSM)

16:55

Chicago Midway (MDW)

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2849

16:20

Des Moines (DSM)

17:40

Chicago Midway (MDW)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2849

16:35

Des Moines (DSM)

17:55

Chicago Midway (MDW)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2849

16:40

Des Moines (DSM)

18:00

Chicago Midway (MDW)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN5088

14:40

Des Moines (DSM)

16:00

Chicago Midway (MDW)

Effective 2026-08-04 through 2026-09-29

Mon
-

Tue

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN5101

14:40

Des Moines (DSM)

16:00

Chicago Midway (MDW)

Effective 2026-08-05 through 2026-09-30

Mon
-

Tue
-

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:20, non-stop
Boeing 737-800 (73H)

A domestic route departing from the Des Moines airport (DSM) and arriving at Chicago Midway airport (MDW).
The flight distance is 305 miles, or 491 km.
The timezone of both the departure and the arrival airports is UTC-6 . Current time at both airports is (loading...).
For direct flights, the flight time varies between 1:15 and 1:25.

Return (MDW-DSM) flights

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