All airlines flying from Denver (DEN) to Chicago Midway (MDW).

FLIGHT SCHEDULE
Direct Flights:
Sun 14:00 Denver (DEN) 17:15 Chicago Midway (MDW) Southwest Airlines WN 2954 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Operates only on 2026-01-04
Sun 06:15 Denver (DEN) 09:40 Chicago Midway (MDW) Southwest Airlines WN 3292 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-09 through 2026-09-27
Sat 17:20 Denver (DEN) 20:45 Chicago Midway (MDW) Southwest Airlines WN 3439 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-08-08 through 2026-09-26
Sat 17:20 Denver (DEN) 20:40 Chicago Midway (MDW) Southwest Airlines WN 3639 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Valid until 2026-01-03
Mon,Thu,Fri 13:25 Denver (DEN) 16:45 Chicago Midway (MDW) Southwest Airlines WN 4232 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 13:25 Denver (DEN) 16:45 Chicago Midway (MDW) Southwest Airlines WN 4232 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-02-20 through 2026-03-01
Sun 17:20 Denver (DEN) 20:45 Chicago Midway (MDW) Southwest Airlines WN 4651 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-05-24
Sun 19:50 Denver (DEN) 23:15 Chicago Midway (MDW) Southwest Airlines WN 4651 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-12 through 2026-05-17
Sun 19:50 Denver (DEN) 23:15 Chicago Midway (MDW) Southwest Airlines WN 4651 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-05-31
Mon,Thu,Fri 20:20 Denver (DEN) 23:40 Chicago Midway (MDW) Southwest Airlines WN 4651 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-04-09 through 2026-06-01
Non-Direct Flights:
Thu,Fri,Sun 11:40 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-01-11 through 2026-01-16
Mon 11:40 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Operates only on 2026-01-19
Sun 11:40 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-01-25 through 2026-02-01
Mon,Thu,Fri 11:40 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-02-05 through 2026-02-09
Tue,Thu,Sun 11:40 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-02-15 through 2026-02-19
Mon 11:40 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-02-23 through 2026-03-02
Sat 11:55 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:05 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 15:40 Denver (DEN) 20:50 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 15:40 Denver (DEN) 20:50 Chicago Midway (MDW) Southwest Airlines WN 256 1-stop Boeing 737-700 (Scimitar Winglets) 4:10 Effective 2026-02-20 through 2026-03-01
Sun 10:25 Denver (DEN) 15:00 Chicago Midway (MDW) Southwest Airlines WN 462 1-stop Boeing 737-700 (Scimitar Winglets) 3:35 Effective 2026-03-08 through 2026-04-05
Sun 13:00 Denver (DEN) 17:45 Chicago Midway (MDW) Southwest Airlines WN 556 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-06-07 through 2026-08-02
Tue,Wed 10:25 Denver (DEN) 16:45 Chicago Midway (MDW) Southwest Airlines WN 693 1-stop Boeing 737-800 (73H) 5:20 Effective 2026-03-10 through 2026-04-01
Wed,Thu 08:00 Denver (DEN) 12:30 Chicago Midway (MDW) Southwest Airlines WN 878 1-stop Boeing 737-700 (73W) 3:30 Valid until 2026-01-01
Mon,Thu,Fri 14:15 Denver (DEN) 19:35 Chicago Midway (MDW) Southwest Airlines WN 1096 1-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-02-05 through 2026-02-09
Tue,Thu,Sun 14:15 Denver (DEN) 19:35 Chicago Midway (MDW) Southwest Airlines WN 1096 1-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-02-15 through 2026-02-19
Mon 14:15 Denver (DEN) 19:35 Chicago Midway (MDW) Southwest Airlines WN 1096 1-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-02-23 through 2026-03-02
Thu,Fri,Sun 14:20 Denver (DEN) 19:45 Chicago Midway (MDW) Southwest Airlines WN 1096 1-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-01-11 through 2026-01-16
Mon,Sun 14:20 Denver (DEN) 19:45 Chicago Midway (MDW) Southwest Airlines WN 1096 1-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-01-19 through 2026-01-25
Sun 14:20 Denver (DEN) 19:45 Chicago Midway (MDW) Southwest Airlines WN 1096 1-stop Boeing 737 MAX 8 (7M8) 4:25 Operates only on 2026-02-01
Tue,Wed 11:45 Denver (DEN) 16:40 Chicago Midway (MDW) Southwest Airlines WN 1207 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 13:20 Denver (DEN) 18:00 Chicago Midway (MDW) Southwest Airlines WN 1228 1-stop Boeing 737-700 (Scimitar Winglets) 3:40 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri,Sun 15:10 Denver (DEN) 20:35 Chicago Midway (MDW) Southwest Airlines WN 1251 1-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-06-04 through 2026-08-03
Sat 12:15 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 1276 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-06-06 through 2026-08-01
Tue,Wed 07:40 Denver (DEN) 12:25 Chicago Midway (MDW) Southwest Airlines WN 1373 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-06-09 through 2026-07-29
Sat 11:40 Denver (DEN) 17:15 Chicago Midway (MDW) Southwest Airlines WN 1459 1-stop Boeing 737-800 (73H) 4:35 Effective 2026-04-11 through 2026-05-30
Tue,Wed 14:20 Denver (DEN) 19:50 Chicago Midway (MDW) Southwest Airlines WN 1459 1-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 15:05 Denver (DEN) 20:30 Chicago Midway (MDW) Southwest Airlines WN 1459 1-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-04-09 through 2026-06-01
Sun 15:15 Denver (DEN) 20:40 Chicago Midway (MDW) Southwest Airlines WN 1459 1-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-04-12 through 2026-05-17
Sun 15:15 Denver (DEN) 20:40 Chicago Midway (MDW) Southwest Airlines WN 1459 1-stop Boeing 737 MAX 8 (7M8) 4:25 Operates only on 2026-05-31
Sat 11:55 Denver (DEN) 16:30 Chicago Midway (MDW) Southwest Airlines WN 1483 1-stop Boeing 737-700 (Scimitar Winglets) 3:35 Operates only on 2026-01-03
Tue,Wed 06:05 Denver (DEN) 12:00 Chicago Midway (MDW) Southwest Airlines WN 1517 1-stop Boeing 737 MAX 8 (7M8) 4:55 Effective 2026-06-09 through 2026-07-29
Sat 12:05 Denver (DEN) 17:00 Chicago Midway (MDW) Southwest Airlines WN 1524 1-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-06-06 through 2026-08-01
Tue,Wed 12:20 Denver (DEN) 17:05 Chicago Midway (MDW) Southwest Airlines WN 1524 1-stop Boeing 737 MAX 8 (7M8) 3:45 Effective 2026-06-09 through 2026-07-29
Sun 12:55 Denver (DEN) 17:35 Chicago Midway (MDW) Southwest Airlines WN 1524 1-stop Boeing 737 MAX 8 (7M8) 3:40 Effective 2026-06-07 through 2026-08-02
Sun 12:20 Denver (DEN) 17:05 Chicago Midway (MDW) Southwest Airlines WN 1535 1-stop Boeing 737-700 (Scimitar Winglets) 3:45 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 13:00 Denver (DEN) 18:05 Chicago Midway (MDW) Southwest Airlines WN 1539 1-stop Boeing 737 MAX 8 (7M8) 4:05 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 07:40 Denver (DEN) 12:20 Chicago Midway (MDW) Southwest Airlines WN 1655 1-stop Boeing 737-800 (73H) 3:40 Effective 2026-06-04 through 2026-08-03
Mon,Tue,Fri,Sun 13:10 Denver (DEN) 17:40 Chicago Midway (MDW) Southwest Airlines WN 1785 1-stop Boeing 737-800 (73H) 3:30 Valid until 2026-01-04
Mon 13:10 Denver (DEN) 17:40 Chicago Midway (MDW) Southwest Airlines WN 1785 1-stop Boeing 737-700 (Scimitar Winglets) 3:30 Operates only on 2026-01-05
Sun 19:05 Denver (DEN) 00:50 Chicago Midway (MDW) Southwest Airlines WN 1849 1-stop Boeing 737 MAX 8 (7M8) 4:45 Effective 2026-04-12 through 2026-05-17 The flight arrives 1 day after departure.

1 2 3 4 5 6

A domestic route departing from the Denver airport (DEN) and arriving at Chicago Midway airport (MDW).
The flight distance is 893 miles, or 1436 km.
The timezone of the departure airport is UTC-7 , and the timezone of the arrival airport is UTC-6 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
For direct flights, the flight time varies between 2:15 and 2:35.

Return (MDW-DEN) flights

Feedback - Disclaimer - Privacy

All airlines flying from Denver (DEN) to Chicago Midway (MDW).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN2954

14:00

Denver (DEN)

17:15

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 WN3292

06:15

Denver (DEN)

09:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN3439

17:20

Denver (DEN)

20:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN3639

17:20

Denver (DEN)

20:40

Chicago Midway (MDW)

Valid until 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4232

13:25

Denver (DEN)

16:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN4232

13:25

Denver (DEN)

16:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4651

17:20

Denver (DEN)

20:45

Chicago Midway (MDW)

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 WN4651

19:50

Denver (DEN)

23:15

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4651

19:50

Denver (DEN)

23:15

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN4651

20:20

Denver (DEN)

23:40

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN256

11:40

Denver (DEN)

17:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN256

11:40

Denver (DEN)

17:00

Chicago Midway (MDW)

Operates only on 2026-01-19

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN256

11:40

Denver (DEN)

17:00

Chicago Midway (MDW)

Effective 2026-01-25 through 2026-02-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN256

11:40

Denver (DEN)

17:00

Chicago Midway (MDW)

Effective 2026-02-05 through 2026-02-09

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN256

11:40

Denver (DEN)

17:00

Chicago Midway (MDW)

Effective 2026-02-15 through 2026-02-19

Mon
-

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN256

11:40

Denver (DEN)

17:00

Chicago Midway (MDW)

Effective 2026-02-23 through 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN256

11:55

Denver (DEN)

17:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:05, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN256

15:40

Denver (DEN)

20:50

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN256

15:40

Denver (DEN)

20:50

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN462

10:25

Denver (DEN)

15:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN556

13:00

Denver (DEN)

17:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN693

10:25

Denver (DEN)

16:45

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 5:20, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN878

08:00

Denver (DEN)

12:30

Chicago Midway (MDW)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:30, 1-stop
Boeing 737-700 (73W)

Non-Direct Flights:

Southwest Airlines WN1096

14:15

Denver (DEN)

19:35

Chicago Midway (MDW)

Effective 2026-02-05 through 2026-02-09

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:20, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1096

14:15

Denver (DEN)

19:35

Chicago Midway (MDW)

Effective 2026-02-15 through 2026-02-19

Mon
-

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun

Duration: 4:20, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1096

14:15

Denver (DEN)

19:35

Chicago Midway (MDW)

Effective 2026-02-23 through 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:20, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1096

14:20

Denver (DEN)

19:45

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1096

14:20

Denver (DEN)

19:45

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1096

14:20

Denver (DEN)

19:45

Chicago Midway (MDW)

Operates only on 2026-02-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1207

11:45

Denver (DEN)

16:40

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1228

13:20

Denver (DEN)

18:00

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:40, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1251

15:10

Denver (DEN)

20:35

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1276

12:15

Denver (DEN)

17:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN1373

07:40

Denver (DEN)

12:25

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN1459

11:40

Denver (DEN)

17:15

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:35, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN1459

14:20

Denver (DEN)

19:50

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:30, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1459

15:05

Denver (DEN)

20:30

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1459

15:15

Denver (DEN)

20:40

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1459

15:15

Denver (DEN)

20:40

Chicago Midway (MDW)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1483

11:55

Denver (DEN)

16:30

Chicago Midway (MDW)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN1517

06:05

Denver (DEN)

12:00

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:55, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1524

12:05

Denver (DEN)

17:00

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, 1-stop
Boeing 737-700 (Scimitar Winglets)

Non-Direct Flights:

Southwest Airlines WN1524

12:20

Denver (DEN)

17:05

Chicago Midway (MDW)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:45, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1524

12:55

Denver (DEN)

17:35

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:40, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1535

12:20

Denver (DEN)

17:05

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Non-Direct Flights:

Southwest Airlines WN1539

13:00

Denver (DEN)

18:05

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:05, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Southwest Airlines WN1655

07:40

Denver (DEN)

12:20

Chicago Midway (MDW)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN1785

13:10

Denver (DEN)

17:40

Chicago Midway (MDW)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:30, 1-stop
Boeing 737-800 (73H)

Non-Direct Flights:

Southwest Airlines WN1785

13:10

Denver (DEN)

17:40

Chicago Midway (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Non-Direct Flights:

Southwest Airlines WN1849

19:05

Denver (DEN)

00:50(+1)

Chicago Midway (MDW)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:45, 1-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

prev Page 5 / 6 next

A domestic route departing from the Denver airport (DEN) and arriving at Chicago Midway airport (MDW).
The flight distance is 893 miles, or 1436 km.
The timezone of the departure airport is UTC-7 , and the timezone of the arrival airport is UTC-6 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
For direct flights, the flight time varies between 2:15 and 2:35.

Return (MDW-DEN) flights

Feedback - Disclaimer - Privacy