All airlines flying from Chicago Midway (MDW) to Dallas Love Field (DAL).

FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 12:30 Chicago Midway (MDW) 14:40 Dallas Love Field (DAL) 1 Southwest Airlines WN 2709 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-08-06 through 2026-09-28
Tue,Wed 15:10 Chicago Midway (MDW) 17:20 Dallas Love Field (DAL) 1 Southwest Airlines WN 2709 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-08-04 through 2026-09-30
Sun 15:40 Chicago Midway (MDW) 17:50 Dallas Love Field (DAL) 1 Southwest Airlines WN 2709 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 16:30 Chicago Midway (MDW) 18:45 Dallas Love Field (DAL) 1 Southwest Airlines WN 2711 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-08-06 through 2026-09-28
Tue,Wed 17:15 Chicago Midway (MDW) 19:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 2711 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-08-04 through 2026-09-30
Sat 18:05 Chicago Midway (MDW) 20:20 Dallas Love Field (DAL) 1 Southwest Airlines WN 2711 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-08-08 through 2026-09-26
Sun 18:45 Chicago Midway (MDW) 20:55 Dallas Love Field (DAL) 1 Southwest Airlines WN 2711 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 12:20 Chicago Midway (MDW) 14:35 Dallas Love Field (DAL) 1 Southwest Airlines WN 2757 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-04 through 2026-08-03
Tue,Wed 13:55 Chicago Midway (MDW) 16:15 Dallas Love Field (DAL) 1 Southwest Airlines WN 2757 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-06-09 through 2026-07-29
Tue,Wed 15:20 Chicago Midway (MDW) 17:35 Dallas Love Field (DAL) 1 Southwest Airlines WN 2758 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 16:20 Chicago Midway (MDW) 18:35 Dallas Love Field (DAL) 1 Southwest Airlines WN 2758 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-04 through 2026-08-03
Sun 17:20 Chicago Midway (MDW) 19:50 Dallas Love Field (DAL) 1 Southwest Airlines WN 2771 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-04-12 through 2026-05-17
Sun 17:20 Chicago Midway (MDW) 19:50 Dallas Love Field (DAL) 1 Southwest Airlines WN 2771 Non-stop Boeing 737-800 (73H) 2:30 Operates only on 2026-05-31
Mon,Thu,Fri 18:15 Chicago Midway (MDW) 20:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 2961 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-04 through 2026-08-03
Sun 19:30 Chicago Midway (MDW) 21:45 Dallas Love Field (DAL) 1 Southwest Airlines WN 2961 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-07 through 2026-08-02
Fri,Sun 13:50 Chicago Midway (MDW) 16:15 Dallas Love Field (DAL) 1 Southwest Airlines WN 2993 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-02 through 2026-01-04
Sat 20:55 Chicago Midway (MDW) 23:10 Dallas Love Field (DAL) 1 Southwest Airlines WN 3024 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-06 through 2026-08-01
Mon,Thu,Fri 19:00 Chicago Midway (MDW) 21:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 3102 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-03-05 through 2026-04-06
Sat 19:00 Chicago Midway (MDW) 21:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 3102 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-03-07 through 2026-04-04
Sun 19:25 Chicago Midway (MDW) 21:55 Dallas Love Field (DAL) 1 Southwest Airlines WN 3102 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-03-08 through 2026-04-05
Tue,Wed 20:35 Chicago Midway (MDW) 23:05 Dallas Love Field (DAL) 1 Southwest Airlines WN 3102 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-03-10 through 2026-04-01
Tue,Wed 06:00 Chicago Midway (MDW) 08:35 Dallas Love Field (DAL) 1 Southwest Airlines WN 3184 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-03-10 through 2026-04-01
Sun 09:50 Chicago Midway (MDW) 12:15 Dallas Love Field (DAL) 1 Southwest Airlines WN 3257 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-12 through 2026-05-17
Sun 09:50 Chicago Midway (MDW) 12:15 Dallas Love Field (DAL) 1 Southwest Airlines WN 3257 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-31
Tue,Wed 10:05 Chicago Midway (MDW) 12:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 3257 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 10:10 Chicago Midway (MDW) 12:35 Dallas Love Field (DAL) 1 Southwest Airlines WN 3257 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-04-09 through 2026-06-01
Sat 10:15 Chicago Midway (MDW) 12:40 Dallas Love Field (DAL) 1 Southwest Airlines WN 3257 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-11 through 2026-05-30
Sun 11:10 Chicago Midway (MDW) 13:35 Dallas Love Field (DAL) 1 Southwest Airlines WN 3257 Non-stop Boeing 737-800 (73H) 2:25 Operates only on 2026-05-24
Sun 13:30 Chicago Midway (MDW) 16:00 Dallas Love Field (DAL) 1 Southwest Airlines WN 3321 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-03-08 through 2026-04-05
Sun 06:50 Chicago Midway (MDW) 09:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 3395 Non-stop Boeing 737-800 (73H) 2:40 Effective 2026-03-08 through 2026-04-05
Mon 09:25 Chicago Midway (MDW) 11:50 Dallas Love Field (DAL) 1 Southwest Airlines WN 3692 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-01-05
Tue,Wed,Sun 11:35 Chicago Midway (MDW) 14:00 Dallas Love Field (DAL) 1 Southwest Airlines WN 3761 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-07 through 2026-05-20
Tue,Wed,Sun 11:35 Chicago Midway (MDW) 14:00 Dallas Love Field (DAL) 1 Southwest Airlines WN 3761 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-05-26 through 2026-06-03
Mon,Thu,Fri 13:10 Chicago Midway (MDW) 15:35 Dallas Love Field (DAL) 1 Southwest Airlines WN 3761 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-09 through 2026-06-01
Sun 14:40 Chicago Midway (MDW) 17:05 Dallas Love Field (DAL) 1 Southwest Airlines WN 3761 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-24
Sat 18:15 Chicago Midway (MDW) 20:40 Dallas Love Field (DAL) 1 Southwest Airlines WN 3765 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-11 through 2026-05-30
Sun 20:30 Chicago Midway (MDW) 22:50 Dallas Love Field (DAL) 1 Southwest Airlines WN 3765 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Operates only on 2026-05-24
Tue,Wed 20:45 Chicago Midway (MDW) 23:10 Dallas Love Field (DAL) 1 Southwest Airlines WN 3765 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-07 through 2026-06-03
Sun 21:05 Chicago Midway (MDW) 23:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 3765 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-04-12 through 2026-05-17
Sun 21:05 Chicago Midway (MDW) 23:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 3765 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-31
Sun 09:55 Chicago Midway (MDW) 12:10 Dallas Love Field (DAL) 1 Southwest Airlines WN 3790 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 06:40 Chicago Midway (MDW) 09:00 Dallas Love Field (DAL) 1 Southwest Airlines WN 3796 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-06-04 through 2026-08-03
Sat 16:35 Chicago Midway (MDW) 19:05 Dallas Love Field (DAL) 1 Southwest Airlines WN 3919 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-03-07 through 2026-04-04
Mon,Thu,Fri 17:00 Chicago Midway (MDW) 19:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 3919 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-03-05 through 2026-04-06
Sun 06:00 Chicago Midway (MDW) 08:10 Dallas Love Field (DAL) 1 Southwest Airlines WN 4025 Non-stop Boeing 737-700 (Scimitar Winglets) 2:10 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 17:45 Chicago Midway (MDW) 20:00 Dallas Love Field (DAL) 1 Southwest Airlines WN 4222 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-08-06 through 2026-09-28
Tue,Wed 19:45 Chicago Midway (MDW) 21:55 Dallas Love Field (DAL) 1 Southwest Airlines WN 4222 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-08-04 through 2026-09-30
Sun 20:05 Chicago Midway (MDW) 22:15 Dallas Love Field (DAL) 1 Southwest Airlines WN 4222 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-08-09 through 2026-09-27
Tue,Wed 11:00 Chicago Midway (MDW) 13:30 Dallas Love Field (DAL) 1 Southwest Airlines WN 4406 Non-stop Boeing 737-700 (Scimitar Winglets) 2:30 Effective 2026-03-10 through 2026-04-01
Mon,Fri 05:15 Chicago Midway (MDW) 07:50 Dallas Love Field (DAL) 1 Southwest Airlines WN 4546 Non-stop Boeing 737-800 (73H) 2:35 Effective 2026-02-13 through 2026-02-20

1 2 3 4 5 6

A domestic route departing from the Chicago Midway airport (MDW) and arriving at Dallas Love Field airport (DAL).
The flight distance is 793 miles, or 1276 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 2:10 and 2:40.

Return (DAL-MDW) flights

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All airlines flying from Chicago Midway (MDW) to Dallas Love Field (DAL).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN2709

12:30

Chicago Midway (MDW)

14:40

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2709

15:10

Chicago Midway (MDW)

17:20

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2709

15:40

Chicago Midway (MDW)

17:50

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2711

16:30

Chicago Midway (MDW)

18:45

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2711

17:15

Chicago Midway (MDW)

19:30

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2711

18:05

Chicago Midway (MDW)

20:20

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2711

18:45

Chicago Midway (MDW)

20:55

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2757

12:20

Chicago Midway (MDW)

14:35

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2757

13:55

Chicago Midway (MDW)

16:15

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2758

15:20

Chicago Midway (MDW)

17:35

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2758

16:20

Chicago Midway (MDW)

18:35

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2771

17:20

Chicago Midway (MDW)

19:50

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2771

17:20

Chicago Midway (MDW)

19:50

Dallas Love Field (DAL) 1

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2961

18:15

Chicago Midway (MDW)

20:30

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2961

19:30

Chicago Midway (MDW)

21:45

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2993

13:50

Chicago Midway (MDW)

16:15

Dallas Love Field (DAL) 1

Effective 2026-01-02 through 2026-01-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3024

20:55

Chicago Midway (MDW)

23:10

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3102

19:00

Chicago Midway (MDW)

21:30

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3102

19:00

Chicago Midway (MDW)

21:30

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3102

19:25

Chicago Midway (MDW)

21:55

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3102

20:35

Chicago Midway (MDW)

23:05

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3184

06:00

Chicago Midway (MDW)

08:35

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3257

09:50

Chicago Midway (MDW)

12:15

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3257

09:50

Chicago Midway (MDW)

12:15

Dallas Love Field (DAL) 1

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3257

10:05

Chicago Midway (MDW)

12:30

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3257

10:10

Chicago Midway (MDW)

12:35

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3257

10:15

Chicago Midway (MDW)

12:40

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3257

11:10

Chicago Midway (MDW)

13:35

Dallas Love Field (DAL) 1

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3321

13:30

Chicago Midway (MDW)

16:00

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3395

06:50

Chicago Midway (MDW)

09:30

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:40, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN3692

09:25

Chicago Midway (MDW)

11:50

Dallas Love Field (DAL) 1

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3761

11:35

Chicago Midway (MDW)

14:00

Dallas Love Field (DAL) 1

Effective 2026-04-07 through 2026-05-20

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3761

11:35

Chicago Midway (MDW)

14:00

Dallas Love Field (DAL) 1

Effective 2026-05-26 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3761

13:10

Chicago Midway (MDW)

15:35

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3761

14:40

Chicago Midway (MDW)

17:05

Dallas Love Field (DAL) 1

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3765

18:15

Chicago Midway (MDW)

20:40

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3765

20:30

Chicago Midway (MDW)

22:50

Dallas Love Field (DAL) 1

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3765

20:45

Chicago Midway (MDW)

23:10

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3765

21:05

Chicago Midway (MDW)

23:30

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3765

21:05

Chicago Midway (MDW)

23:30

Dallas Love Field (DAL) 1

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3790

09:55

Chicago Midway (MDW)

12:10

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3796

06:40

Chicago Midway (MDW)

09:00

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN3919

16:35

Chicago Midway (MDW)

19:05

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3919

17:00

Chicago Midway (MDW)

19:30

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4025

06:00

Chicago Midway (MDW)

08:10

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4222

17:45

Chicago Midway (MDW)

20:00

Dallas Love Field (DAL) 1

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4222

19:45

Chicago Midway (MDW)

21:55

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4222

20:05

Chicago Midway (MDW)

22:15

Dallas Love Field (DAL) 1

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN4406

11:00

Chicago Midway (MDW)

13:30

Dallas Love Field (DAL) 1

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN4546

05:15

Chicago Midway (MDW)

07:50

Dallas Love Field (DAL) 1

Effective 2026-02-13 through 2026-02-20

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 2:35, non-stop
Boeing 737-800 (73H)

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A domestic route departing from the Chicago Midway airport (MDW) and arriving at Dallas Love Field airport (DAL).
The flight distance is 793 miles, or 1276 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 2:10 and 2:40.

Return (DAL-MDW) flights

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