All airlines flying from Milwaukee (MKE) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Direct Flights:
Sat 05:40 Milwaukee (MKE) 06:35 Chicago Midway (MDW) Southwest Airlines WN 353 Non-stop Boeing 737-800 (73H) 0:55 Effective 2026-04-11 through 2026-05-30
Tue,Wed 05:50 Milwaukee (MKE) 06:45 Chicago Midway (MDW) Southwest Airlines WN 353 Non-stop Boeing 737-800 (73H) 0:55 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri,Sun 05:50 Milwaukee (MKE) 06:45 Chicago Midway (MDW) Southwest Airlines WN 353 Non-stop Boeing 737-700 (Scimitar Winglets) 0:55 Effective 2026-04-09 through 2026-05-22
Mon,Thu,Fri,Sun 05:50 Milwaukee (MKE) 06:45 Chicago Midway (MDW) Southwest Airlines WN 353 Non-stop Boeing 737-700 (Scimitar Winglets) 0:55 Effective 2026-05-25 through 2026-06-01
Sun 07:10 Milwaukee (MKE) 08:00 Chicago Midway (MDW) Southwest Airlines WN 353 Non-stop Boeing 737 MAX 8 (7M8) 0:50 Operates only on 2026-05-24
Mon,Thu,Fri 05:45 Milwaukee (MKE) 06:30 Chicago Midway (MDW) Southwest Airlines WN 803 Non-stop Boeing 737 MAX 8 (7M8) 0:45 Effective 2026-08-06 through 2026-09-28
Sun 16:45 Milwaukee (MKE) 17:35 Chicago Midway (MDW) Southwest Airlines WN 1734 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-06-07 through 2026-08-02
Sat 14:00 Milwaukee (MKE) 14:45 Chicago Midway (MDW) Southwest Airlines WN 1753 Non-stop Boeing 737-700 (Scimitar Winglets) 0:45 Effective 2026-04-11 through 2026-05-30
Tue,Wed 16:10 Milwaukee (MKE) 17:00 Chicago Midway (MDW) Southwest Airlines WN 1919 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-03-10 through 2026-04-01
Sat 16:50 Milwaukee (MKE) 17:40 Chicago Midway (MDW) Southwest Airlines WN 1919 Non-stop Boeing 737-800 (73H) 0:50 Effective 2026-03-07 through 2026-04-04
Sun 05:45 Milwaukee (MKE) 06:45 Chicago Midway (MDW) Southwest Airlines WN 1980 Non-stop Boeing 737-800 (73H) 1:00 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 05:50 Milwaukee (MKE) 06:50 Chicago Midway (MDW) Southwest Airlines WN 1980 Non-stop Boeing 737 MAX 8 (7M8) 1:00 Effective 2026-03-05 through 2026-04-06
Tue,Wed,Sat 05:50 Milwaukee (MKE) 06:50 Chicago Midway (MDW) Southwest Airlines WN 1980 Non-stop Boeing 737-700 (Scimitar Winglets) 1:00 Effective 2026-03-07 through 2026-04-04
Tue,Wed 16:05 Milwaukee (MKE) 16:55 Chicago Midway (MDW) Southwest Airlines WN 2385 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-04-07 through 2026-06-03
Sun 16:05 Milwaukee (MKE) 16:55 Chicago Midway (MDW) Southwest Airlines WN 2385 Non-stop Boeing 737 MAX 8 (7M8) 0:50 Operates only on 2026-05-24
Mon,Thu,Fri 16:50 Milwaukee (MKE) 17:40 Chicago Midway (MDW) Southwest Airlines WN 2385 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-04-09 through 2026-06-01
Sun 17:10 Milwaukee (MKE) 18:00 Chicago Midway (MDW) Southwest Airlines WN 2385 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-04-12 through 2026-05-17
Sun 17:10 Milwaukee (MKE) 18:00 Chicago Midway (MDW) Southwest Airlines WN 2385 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Operates only on 2026-05-31
Tue,Wed 15:50 Milwaukee (MKE) 16:40 Chicago Midway (MDW) Southwest Airlines WN 2886 Non-stop Boeing 737-800 (73H) 0:50 Effective 2026-08-04 through 2026-09-30
Sun 16:00 Milwaukee (MKE) 16:50 Chicago Midway (MDW) Southwest Airlines WN 2886 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-08-09 through 2026-09-27
Sat 16:00 Milwaukee (MKE) 16:50 Chicago Midway (MDW) Southwest Airlines WN 2909 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-06-06 through 2026-08-01
Tue,Wed 16:10 Milwaukee (MKE) 17:00 Chicago Midway (MDW) Southwest Airlines WN 2953 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 17:15 Milwaukee (MKE) 18:05 Chicago Midway (MDW) Southwest Airlines WN 2953 Non-stop Boeing 737-800 (73H) 0:50 Effective 2026-06-04 through 2026-08-03
Sat 05:45 Milwaukee (MKE) 06:35 Chicago Midway (MDW) Southwest Airlines WN 3178 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 05:50 Milwaukee (MKE) 06:40 Chicago Midway (MDW) Southwest Airlines WN 3178 Non-stop Boeing 737-800 (73H) 0:50 Effective 2026-06-04 through 2026-08-03
Sun 06:00 Milwaukee (MKE) 06:50 Chicago Midway (MDW) Southwest Airlines WN 3178 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-06-07 through 2026-08-02
Tue,Wed 06:00 Milwaukee (MKE) 06:50 Chicago Midway (MDW) Southwest Airlines WN 3178 Non-stop Boeing 737 MAX 8 (7M8) 0:50 Effective 2026-06-09 through 2026-07-29
Sun 16:40 Milwaukee (MKE) 17:30 Chicago Midway (MDW) Southwest Airlines WN 3326 Non-stop Boeing 737-700 (Scimitar Winglets) 0:50 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 16:55 Milwaukee (MKE) 17:45 Chicago Midway (MDW) Southwest Airlines WN 3572 Non-stop Boeing 737 MAX 8 (7M8) 0:50 Effective 2026-03-05 through 2026-04-06
Sat 13:30 Milwaukee (MKE) 14:20 Chicago Midway (MDW) Southwest Airlines WN 3641 Non-stop Boeing 737 MAX 8 (7M8) 0:50 Effective 2026-08-08 through 2026-09-26
Sat 05:45 Milwaukee (MKE) 06:30 Chicago Midway (MDW) Southwest Airlines WN 4159 Non-stop Boeing 737-700 (Scimitar Winglets) 0:45 Effective 2026-08-08 through 2026-09-26
Sun 05:45 Milwaukee (MKE) 06:30 Chicago Midway (MDW) Southwest Airlines WN 4159 Non-stop Boeing 737 MAX 8 (7M8) 0:45 Effective 2026-08-09 through 2026-09-27
Tue,Wed 06:40 Milwaukee (MKE) 07:30 Chicago Midway (MDW) Southwest Airlines WN 4159 Non-stop Boeing 737-800 (73H) 0:50 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 16:25 Milwaukee (MKE) 17:15 Chicago Midway (MDW) Southwest Airlines WN 4159 Non-stop Boeing 737 MAX 8 (7M8) 0:50 Effective 2026-08-06 through 2026-09-28

A domestic route departing from the Milwaukee airport (MKE) and arriving at Chicago Midway airport (MDW).
The flight distance is 81 miles, or 130 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 0:45 and 1:00.

Return (MDW-MKE) flights

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All airlines flying from Milwaukee (MKE) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN353

05:40

Milwaukee (MKE)

06:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 0:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN353

05:50

Milwaukee (MKE)

06:45

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 0:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN353

05:50

Milwaukee (MKE)

06:45

Chicago Midway (MDW)

Effective 2026-04-09 through 2026-05-22

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 0:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN353

05:50

Milwaukee (MKE)

06:45

Chicago Midway (MDW)

Effective 2026-05-25 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 0:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN353

07:10

Milwaukee (MKE)

08:00

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN803

05:45

Milwaukee (MKE)

06:30

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 0:45, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1734

16:45

Milwaukee (MKE)

17:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1753

14:00

Milwaukee (MKE)

14:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 0:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1919

16:10

Milwaukee (MKE)

17:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1919

16:50

Milwaukee (MKE)

17:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 0:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1980

05:45

Milwaukee (MKE)

06:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:00, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1980

05:50

Milwaukee (MKE)

06:50

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1980

05:50

Milwaukee (MKE)

06:50

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:00, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2385

16:05

Milwaukee (MKE)

16:55

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2385

16:05

Milwaukee (MKE)

16:55

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2385

16:50

Milwaukee (MKE)

17:40

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2385

17:10

Milwaukee (MKE)

18:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2385

17:10

Milwaukee (MKE)

18:00

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2886

15:50

Milwaukee (MKE)

16:40

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2886

16:00

Milwaukee (MKE)

16:50

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2909

16:00

Milwaukee (MKE)

16:50

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2953

16:10

Milwaukee (MKE)

17:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2953

17:15

Milwaukee (MKE)

18:05

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3178

05:45

Milwaukee (MKE)

06:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3178

05:50

Milwaukee (MKE)

06:40

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3178

06:00

Milwaukee (MKE)

06:50

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3178

06:00

Milwaukee (MKE)

06:50

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3326

16:40

Milwaukee (MKE)

17:30

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:50, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3572

16:55

Milwaukee (MKE)

17:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3641

13:30

Milwaukee (MKE)

14:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 0:50, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4159

05:45

Milwaukee (MKE)

06:30

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 0:45, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4159

05:45

Milwaukee (MKE)

06:30

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 0:45, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4159

06:40

Milwaukee (MKE)

07:30

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4159

16:25

Milwaukee (MKE)

17:15

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 0:50, non-stop
Boeing 737 MAX 8 (7M8)

A domestic route departing from the Milwaukee airport (MKE) and arriving at Chicago Midway airport (MDW).
The flight distance is 81 miles, or 130 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 0:45 and 1:00.

Return (MDW-MKE) flights

Feedback - Disclaimer - Privacy