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

FLIGHT SCHEDULE
Direct Flights:
Mon-Fri 18:30 Dallas Love Field (DAL) 1 20:40 Chicago Midway (MDW) Southwest Airlines WN 1327 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-01-26 through 2026-02-04
Sun 18:30 Dallas Love Field (DAL) 1 20:40 Chicago Midway (MDW) Southwest Airlines WN 1327 Non-stop Boeing 737-800 (73H) 2:10 Operates only on 2026-02-08
Tue,Wed 18:30 Dallas Love Field (DAL) 1 20:40 Chicago Midway (MDW) Southwest Airlines WN 1327 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-02-10 through 2026-02-11
Tue,Wed 18:30 Dallas Love Field (DAL) 1 20:40 Chicago Midway (MDW) Southwest Airlines WN 1327 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-02-18 through 2026-03-04
Thu,Fri,Sun 19:45 Dallas Love Field (DAL) 1 21:55 Chicago Midway (MDW) Southwest Airlines WN 1327 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-01-11 through 2026-01-16
Mon,Sun 19:45 Dallas Love Field (DAL) 1 21:55 Chicago Midway (MDW) Southwest Airlines WN 1327 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-01-19 through 2026-01-25
Sun 19:45 Dallas Love Field (DAL) 1 21:55 Chicago Midway (MDW) Southwest Airlines WN 1327 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Operates only on 2026-02-01
Sun 19:45 Dallas Love Field (DAL) 1 21:55 Chicago Midway (MDW) Southwest Airlines WN 1327 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-08-09 through 2026-09-27
Sat 09:40 Dallas Love Field (DAL) 1 11:50 Chicago Midway (MDW) Southwest Airlines WN 1328 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-08-08 through 2026-09-26
Tue,Wed 09:50 Dallas Love Field (DAL) 1 12:00 Chicago Midway (MDW) Southwest Airlines WN 1328 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-08-04 through 2026-09-30
Sun 10:40 Dallas Love Field (DAL) 1 12:50 Chicago Midway (MDW) Southwest Airlines WN 1328 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 18:10 Dallas Love Field (DAL) 1 20:20 Chicago Midway (MDW) Southwest Airlines WN 1328 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-08-06 through 2026-09-28
Sun 20:45 Dallas Love Field (DAL) 1 22:55 Chicago Midway (MDW) Southwest Airlines WN 1329 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-06-07 through 2026-08-02
Mon,Thu-Sat 06:00 Dallas Love Field (DAL) 1 08:15 Chicago Midway (MDW) Southwest Airlines WN 1355 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-04 through 2026-08-03
Sun 06:10 Dallas Love Field (DAL) 1 08:25 Chicago Midway (MDW) Southwest Airlines WN 1355 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 08:30 Dallas Love Field (DAL) 1 10:45 Chicago Midway (MDW) Southwest Airlines WN 1356 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 10:05 Dallas Love Field (DAL) 1 12:20 Chicago Midway (MDW) Southwest Airlines WN 1357 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-04 through 2026-08-03
Tue,Wed 12:25 Dallas Love Field (DAL) 1 14:40 Chicago Midway (MDW) Southwest Airlines WN 1357 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-06-09 through 2026-07-29
Sun 13:10 Dallas Love Field (DAL) 1 15:25 Chicago Midway (MDW) Southwest Airlines WN 1358 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 14:05 Dallas Love Field (DAL) 1 16:20 Chicago Midway (MDW) Southwest Airlines WN 1358 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-04 through 2026-08-03
Tue,Wed 15:00 Dallas Love Field (DAL) 1 17:15 Chicago Midway (MDW) Southwest Airlines WN 1358 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-06-09 through 2026-07-29
Sun 15:50 Dallas Love Field (DAL) 1 18:05 Chicago Midway (MDW) Southwest Airlines WN 1359 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-07 through 2026-08-02
Tue,Wed 21:55 Dallas Love Field (DAL) 1 00:05 Chicago Midway (MDW) Southwest Airlines WN 1359 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-06-09 through 2026-07-29 The flight arrives 1 day after departure.
Mon,Thu,Fri 22:50 Dallas Love Field (DAL) 1 01:00 Chicago Midway (MDW) Southwest Airlines WN 1359 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-06-04 through 2026-08-03 The flight arrives 1 day after departure.
Thu 18:40 Dallas Love Field (DAL) 1 20:50 Chicago Midway (MDW) Southwest Airlines WN 1414 Non-stop Boeing 737-800 (73H) 2:10 Valid until 2026-01-01
Sun 13:00 Dallas Love Field (DAL) 1 15:10 Chicago Midway (MDW) Southwest Airlines WN 1478 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-03-08 through 2026-04-05
Tue,Wed 09:45 Dallas Love Field (DAL) 1 12:00 Chicago Midway (MDW) Southwest Airlines WN 1517 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-06-09 through 2026-07-29
Mon 07:20 Dallas Love Field (DAL) 1 09:35 Chicago Midway (MDW) Southwest Airlines WN 1522 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-01-05
Wed,Thu 10:30 Dallas Love Field (DAL) 1 12:40 Chicago Midway (MDW) Southwest Airlines WN 1522 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Valid until 2026-01-01
Tue,Wed 14:45 Dallas Love Field (DAL) 1 17:00 Chicago Midway (MDW) Southwest Airlines WN 1538 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-04-07 through 2026-06-03
Sun 14:50 Dallas Love Field (DAL) 1 17:05 Chicago Midway (MDW) Southwest Airlines WN 1538 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-05-24
Sat 15:15 Dallas Love Field (DAL) 1 17:30 Chicago Midway (MDW) Southwest Airlines WN 1538 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-04-11 through 2026-05-30
Sun 15:45 Dallas Love Field (DAL) 1 18:00 Chicago Midway (MDW) Southwest Airlines WN 1538 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-04-12 through 2026-05-17
Sun 15:45 Dallas Love Field (DAL) 1 18:00 Chicago Midway (MDW) Southwest Airlines WN 1538 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2026-05-31
Sun 18:25 Dallas Love Field (DAL) 1 20:40 Chicago Midway (MDW) Southwest Airlines WN 1542 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Operates only on 2026-05-24
Sat 18:55 Dallas Love Field (DAL) 1 21:05 Chicago Midway (MDW) Southwest Airlines WN 1561 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-03-07 through 2026-04-04
Tue,Wed 19:10 Dallas Love Field (DAL) 1 21:20 Chicago Midway (MDW) Southwest Airlines WN 1561 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 19:50 Dallas Love Field (DAL) 1 22:00 Chicago Midway (MDW) Southwest Airlines WN 1561 Non-stop Boeing 737-700 (Scimitar Winglets) 2:10 Effective 2026-03-05 through 2026-04-06
Sun 19:50 Dallas Love Field (DAL) 1 22:00 Chicago Midway (MDW) Southwest Airlines WN 1561 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 21:45 Dallas Love Field (DAL) 1 23:55 Chicago Midway (MDW) Southwest Airlines WN 1594 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-04-09 through 2026-06-01
Fri 22:35 Dallas Love Field (DAL) 1 00:45 Chicago Midway (MDW) Southwest Airlines WN 1595 Non-stop Boeing 737-700 (Scimitar Winglets) 2:10 Operates only on 2026-01-02 The flight arrives 1 day after departure.
Sun 22:55 Dallas Love Field (DAL) 1 01:05 Chicago Midway (MDW) Southwest Airlines WN 1595 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Operates only on 2026-01-04 The flight arrives 1 day after departure.
Sat 14:30 Dallas Love Field (DAL) 1 16:45 Chicago Midway (MDW) Southwest Airlines WN 1776 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Valid until 2026-01-03
Sun 14:35 Dallas Love Field (DAL) 1 16:50 Chicago Midway (MDW) Southwest Airlines WN 1776 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2026-01-04
Sun 20:10 Dallas Love Field (DAL) 1 22:20 Chicago Midway (MDW) Southwest Airlines WN 1849 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Operates only on 2026-05-24
Sun 22:40 Dallas Love Field (DAL) 1 00:50 Chicago Midway (MDW) Southwest Airlines WN 1849 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Effective 2026-04-12 through 2026-05-17 The flight arrives 1 day after departure.
Sun 22:40 Dallas Love Field (DAL) 1 00:50 Chicago Midway (MDW) Southwest Airlines WN 1849 Non-stop Boeing 737 MAX 8 (7M8) 2:10 Operates only on 2026-05-31 The flight arrives 1 day after departure.
Thu,Fri,Sun 12:45 Dallas Love Field (DAL) 1 14:55 Chicago Midway (MDW) Southwest Airlines WN 1880 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-01-11 through 2026-01-16
Mon,Sun 12:45 Dallas Love Field (DAL) 1 14:55 Chicago Midway (MDW) Southwest Airlines WN 1880 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 12:45 Dallas Love Field (DAL) 1 14:55 Chicago Midway (MDW) Southwest Airlines WN 1880 Non-stop Boeing 737-800 (73H) 2:10 Effective 2026-02-01 through 2026-02-06

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

Feedback - Disclaimer - Privacy

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN1327

18:30

Dallas Love Field (DAL) 1

20:40

Chicago Midway (MDW)

Effective 2026-01-26 through 2026-02-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1327

18:30

Dallas Love Field (DAL) 1

20:40

Chicago Midway (MDW)

Operates only on 2026-02-08

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1327

18:30

Dallas Love Field (DAL) 1

20:40

Chicago Midway (MDW)

Effective 2026-02-10 through 2026-02-11

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1327

18:30

Dallas Love Field (DAL) 1

20:40

Chicago Midway (MDW)

Effective 2026-02-18 through 2026-03-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1327

19:45

Dallas Love Field (DAL) 1

21:55

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1327

19:45

Dallas Love Field (DAL) 1

21:55

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1327

19:45

Dallas Love Field (DAL) 1

21:55

Chicago Midway (MDW)

Operates only on 2026-02-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1327

19:45

Dallas Love Field (DAL) 1

21:55

Chicago Midway (MDW)

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 WN1328

09:40

Dallas Love Field (DAL) 1

11:50

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1328

09:50

Dallas Love Field (DAL) 1

12:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1328

10:40

Dallas Love Field (DAL) 1

12:50

Chicago Midway (MDW)

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 WN1328

18:10

Dallas Love Field (DAL) 1

20:20

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1329

20:45

Dallas Love Field (DAL) 1

22:55

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1355

06:00

Dallas Love Field (DAL) 1

08:15

Chicago Midway (MDW)

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 WN1355

06:10

Dallas Love Field (DAL) 1

08:25

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1356

08:30

Dallas Love Field (DAL) 1

10:45

Chicago Midway (MDW)

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 WN1357

10:05

Dallas Love Field (DAL) 1

12:20

Chicago Midway (MDW)

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 WN1357

12:25

Dallas Love Field (DAL) 1

14:40

Chicago Midway (MDW)

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 WN1358

13:10

Dallas Love Field (DAL) 1

15:25

Chicago Midway (MDW)

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 WN1358

14:05

Dallas Love Field (DAL) 1

16:20

Chicago Midway (MDW)

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 WN1358

15:00

Dallas Love Field (DAL) 1

17:15

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1359

15:50

Dallas Love Field (DAL) 1

18:05

Chicago Midway (MDW)

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 WN1359

21:55

Dallas Love Field (DAL) 1

00:05(+1)

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN1359

22:50

Dallas Love Field (DAL) 1

01:00(+1)

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN1414

18:40

Dallas Love Field (DAL) 1

20:50

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1478

13:00

Dallas Love Field (DAL) 1

15:10

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1517

09:45

Dallas Love Field (DAL) 1

12:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1522

07:20

Dallas Love Field (DAL) 1

09:35

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1522

10:30

Dallas Love Field (DAL) 1

12:40

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1538

14:45

Dallas Love Field (DAL) 1

17:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1538

14:50

Dallas Love Field (DAL) 1

17:05

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1538

15:15

Dallas Love Field (DAL) 1

17:30

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1538

15:45

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

Direct Flights:

Southwest Airlines WN1538

15:45

Dallas Love Field (DAL) 1

18:00

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1542

18:25

Dallas Love Field (DAL) 1

20:40

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1561

18:55

Dallas Love Field (DAL) 1

21:05

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1561

19:10

Dallas Love Field (DAL) 1

21:20

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1561

19:50

Dallas Love Field (DAL) 1

22:00

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1561

19:50

Dallas Love Field (DAL) 1

22:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1594

21:45

Dallas Love Field (DAL) 1

23:55

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1595

22:35

Dallas Love Field (DAL) 1

00:45(+1)

Chicago Midway (MDW)

Operates only on 2026-01-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 2:10, non-stop
Boeing 737-700 (Scimitar Winglets)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN1595

22:55

Dallas Love Field (DAL) 1

01:05(+1)

Chicago Midway (MDW)

Operates only on 2026-01-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN1776

14:30

Dallas Love Field (DAL) 1

16:45

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN1776

14:35

Dallas Love Field (DAL) 1

16:50

Chicago Midway (MDW)

Operates only on 2026-01-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1849

20:10

Dallas Love Field (DAL) 1

22:20

Chicago Midway (MDW)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1849

22:40

Dallas Love Field (DAL) 1

00:50(+1)

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN1849

22:40

Dallas Love Field (DAL) 1

00:50(+1)

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 2:10, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN1880

12:45

Dallas Love Field (DAL) 1

14:55

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1880

12:45

Dallas Love Field (DAL) 1

14:55

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN1880

12:45

Dallas Love Field (DAL) 1

14:55

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

prev Page 3 / 6 next

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