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

FLIGHT SCHEDULE
Non-Direct Flights:
Mon,Thu,Fri 14:20 Dallas Love Field (DAL) 1 18:00 Chicago Midway (MDW) Southwest Airlines WN 3180 1-stop Boeing 737-800 (73H) 3:40 Effective 2026-03-05 through 2026-04-06
Sat 12:55 Dallas Love Field (DAL) 1 16:25 Chicago Midway (MDW) Southwest Airlines WN 3216 1-stop Boeing 737-700 (Scimitar Winglets) 3:30 Effective 2026-01-10 through 2026-02-07
Sat 15:30 Dallas Love Field (DAL) 1 19:50 Chicago Midway (MDW) Southwest Airlines WN 3384 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Operates only on 2026-01-03
Sat 13:20 Dallas Love Field (DAL) 1 17:05 Chicago Midway (MDW) Southwest Airlines WN 3444 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-03-07 through 2026-04-04
Tue,Wed 06:50 Dallas Love Field (DAL) 1 10:25 Chicago Midway (MDW) Southwest Airlines WN 3816 1-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-03-10 through 2026-04-01
Sat 12:30 Dallas Love Field (DAL) 1 17:10 Chicago Midway (MDW) Southwest Airlines WN 3850 1-stop Boeing 737 MAX 8 (7M8) 4:40 Effective 2026-04-11 through 2026-05-30
Mon,Thu,Fri 08:00 Dallas Love Field (DAL) 1 12:10 Chicago Midway (MDW) Southwest Airlines WN 4386 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-06-04 through 2026-08-03
Sat 08:00 Dallas Love Field (DAL) 1 12:35 Chicago Midway (MDW) Southwest Airlines WN 4580 1-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-03-07 through 2026-04-04
Sat 12:25 Dallas Love Field (DAL) 1 16:30 Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-800 (73H) 4:05 Effective 2026-01-10 through 2026-01-31
Sat 12:25 Dallas Love Field (DAL) 1 16:15 Chicago Midway (MDW) Southwest Airlines WN 4990 1-stop Boeing 737-800 (73H) 3:50 Operates only on 2026-02-07
Sat 11:15 Dallas Love Field (DAL) 1 17:10 Chicago Midway (MDW) Southwest Airlines WN 17 2-stop Boeing 737-700 (Scimitar Winglets) 5:55 Effective 2026-02-14 through 2026-02-28
Sat 13:05 Dallas Love Field (DAL) 1 19:20 Chicago Midway (MDW) Southwest Airlines WN 66 2-stop Boeing 737-700 (Scimitar Winglets) 6:15 Effective 2026-06-06 through 2026-08-01
Thu,Fri,Sun 14:05 Dallas Love Field (DAL) 1 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 2-stop Boeing 737-700 (Scimitar Winglets) 6:05 Effective 2026-01-11 through 2026-01-16
Mon,Sun 14:05 Dallas Love Field (DAL) 1 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 2-stop Boeing 737-700 (Scimitar Winglets) 6:05 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 14:05 Dallas Love Field (DAL) 1 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 2-stop Boeing 737-700 (Scimitar Winglets) 6:05 Effective 2026-02-01 through 2026-02-06
Mon,Sun 14:05 Dallas Love Field (DAL) 1 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 2-stop Boeing 737-700 (Scimitar Winglets) 6:05 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 14:05 Dallas Love Field (DAL) 1 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 2-stop Boeing 737-700 (Scimitar Winglets) 6:05 Effective 2026-02-17 through 2026-02-23
Mon 14:05 Dallas Love Field (DAL) 1 20:10 Chicago Midway (MDW) Southwest Airlines WN 309 2-stop Boeing 737-700 (Scimitar Winglets) 6:05 Operates only on 2026-03-02
Tue,Wed 06:15 Dallas Love Field (DAL) 1 15:50 Chicago Midway (MDW) Southwest Airlines WN 1713 2-stop Boeing 737 MAX 8 (7M8) 9:35 Effective 2026-03-10 through 2026-04-01
Sun 06:00 Dallas Love Field (DAL) 1 13:05 Chicago Midway (MDW) Southwest Airlines WN 2072 2-stop Boeing 737-700 (Scimitar Winglets) 7:05 Effective 2026-04-12 through 2026-05-17
Sun 06:00 Dallas Love Field (DAL) 1 13:05 Chicago Midway (MDW) Southwest Airlines WN 2072 2-stop Boeing 737-700 (Scimitar Winglets) 7:05 Operates only on 2026-05-31
Tue,Wed 12:00 Dallas Love Field (DAL) 1 17:00 Chicago Midway (MDW) Southwest Airlines WN 2953 2-stop Boeing 737-700 (Scimitar Winglets) 5:00 Effective 2026-06-09 through 2026-07-29
Sat 11:10 Dallas Love Field (DAL) 1 16:45 Chicago Midway (MDW) Southwest Airlines WN 4145 2-stop Boeing 737-700 (Scimitar Winglets) 5:35 Effective 2026-01-10 through 2026-02-07
Mon,Thu,Fri 13:00 Dallas Love Field (DAL) 1 20:45 Chicago Midway (MDW) Southwest Airlines WN 4569 2-stop Boeing 737-700 (Scimitar Winglets) 7:45 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 13:00 Dallas Love Field (DAL) 1 20:45 Chicago Midway (MDW) Southwest Airlines WN 4569 2-stop Boeing 737-700 (Scimitar Winglets) 7:45 Effective 2026-02-20 through 2026-03-01
Mon 08:20 Dallas Love Field (DAL) 1 19:05 Chicago Midway (MDW) Southwest Airlines WN 1419 3-stop Boeing 737-700 (Scimitar Winglets) 10:45 Operates only on 2026-01-05
Sun 08:00 Dallas Love Field (DAL) 1 18:00 Chicago Midway (MDW) Southwest Airlines WN 2157 3-stop Boeing 737-700 (Scimitar Winglets) 10:00 Effective 2026-04-12 through 2026-05-17
Sun 08:00 Dallas Love Field (DAL) 1 18:00 Chicago Midway (MDW) Southwest Airlines WN 2157 3-stop Boeing 737-700 (Scimitar Winglets) 10:00 Operates only on 2026-05-31
Sun 07:10 Dallas Love Field (DAL) 1 17:15 Chicago Midway (MDW) Southwest Airlines WN 4061 3-stop Boeing 737-700 (Scimitar Winglets) 10:05 Effective 2026-03-08 through 2026-04-05

1 2 3 4 5 6

A domestic route departing from the Dallas Love Field airport (DAL) and arriving at Chicago Midway airport (MDW).
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 2:05 and 2:15.

Return (MDW-DAL) flights

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

FLIGHT SCHEDULE

Non-Direct Flights:

Southwest Airlines WN3180

14:20

Dallas Love Field (DAL) 1

18:00

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:40, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN3216

12:55

Dallas Love Field (DAL) 1

16:25

Chicago Midway (MDW)

Effective 2026-01-10 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:30, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3384

15:30

Dallas Love Field (DAL) 1

19:50

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:20, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3444

13:20

Dallas Love Field (DAL) 1

17:05

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:45, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3816

06:50

Dallas Love Field (DAL) 1

10:25

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:35, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN3850

12:30

Dallas Love Field (DAL) 1

17:10

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:40, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4386

08:00

Dallas Love Field (DAL) 1

12:10

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:10, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4580

08:00

Dallas Love Field (DAL) 1

12:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:35, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN4990

12:25

Dallas Love Field (DAL) 1

16:30

Chicago Midway (MDW)

Effective 2026-01-10 through 2026-01-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:05, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN4990

12:25

Dallas Love Field (DAL) 1

16:15

Chicago Midway (MDW)

Operates only on 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:50, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN17

11:15

Dallas Love Field (DAL) 1

17:10

Chicago Midway (MDW)

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:55, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN66

13:05

Dallas Love Field (DAL) 1

19:20

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 6:15, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

14:05

Dallas Love Field (DAL) 1

20:10

Chicago Midway (MDW)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 6:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

14:05

Dallas Love Field (DAL) 1

20:10

Chicago Midway (MDW)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

14:05

Dallas Love Field (DAL) 1

20:10

Chicago Midway (MDW)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 6:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

14:05

Dallas Love Field (DAL) 1

20:10

Chicago Midway (MDW)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 6:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

14:05

Dallas Love Field (DAL) 1

20:10

Chicago Midway (MDW)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 6:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN309

14:05

Dallas Love Field (DAL) 1

20:10

Chicago Midway (MDW)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 6:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1713

06:15

Dallas Love Field (DAL) 1

15:50

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 9:35, 2-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN2072

06:00

Dallas Love Field (DAL) 1

13:05

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2072

06:00

Dallas Love Field (DAL) 1

13:05

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 7:05, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2953

12:00

Dallas Love Field (DAL) 1

17:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:00, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4145

11:10

Dallas Love Field (DAL) 1

16:45

Chicago Midway (MDW)

Effective 2026-01-10 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 5:35, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4569

13:00

Dallas Love Field (DAL) 1

20:45

Chicago Midway (MDW)

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 7:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4569

13:00

Dallas Love Field (DAL) 1

20:45

Chicago Midway (MDW)

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 7:45, 2-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1419

08:20

Dallas Love Field (DAL) 1

19:05

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 10:45, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2157

08:00

Dallas Love Field (DAL) 1

18:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:00, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN2157

08:00

Dallas Love Field (DAL) 1

18:00

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:00, 3-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN4061

07:10

Dallas Love Field (DAL) 1

17:15

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 10:05, 3-stop
Boeing 737-700 (Scimitar Winglets)

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A domestic route departing from the Dallas Love Field airport (DAL) and arriving at Chicago Midway airport (MDW).
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 2:05 and 2:15.

Return (MDW-DAL) flights

Feedback - Disclaimer - Privacy