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

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Thu 08:00 Denver (DEN) 11:25 Chicago Midway (MDW)
Southwest Airlines WN 1339 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Operates only on 2026-01-01
Tue,Wed 11:00 Denver (DEN) 14:20 Chicago Midway (MDW)
Southwest Airlines WN 1428 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-08-04 through 2026-09-30
Sat 11:10 Denver (DEN) 14:30 Chicago Midway (MDW)
Southwest Airlines WN 1428 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-08 through 2026-09-26
Mon,Thu,Fri 12:50 Denver (DEN) 16:10 Chicago Midway (MDW)
Southwest Airlines WN 1428 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-06 through 2026-09-28
Sun 14:55 Denver (DEN) 18:15 Chicago Midway (MDW)
Southwest Airlines WN 1428 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-09 through 2026-09-27
Tue,Wed 13:25 Denver (DEN) 16:40 Chicago Midway (MDW)
Southwest Airlines WN 1447 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-03-10 through 2026-04-01
Sat 14:30 Denver (DEN) 17:45 Chicago Midway (MDW)
Southwest Airlines WN 1447 Non-stop Boeing 737-700 (Scimitar Winglets) 2:15 Effective 2026-03-07 through 2026-04-04
Sun 14:35 Denver (DEN) 17:50 Chicago Midway (MDW)
Southwest Airlines WN 1447 Non-stop Boeing 737-800 (73H) 2:15 Effective 2026-03-08 through 2026-04-05
Thu,Fri 14:40 Denver (DEN) 17:55 Chicago Midway (MDW)
Southwest Airlines WN 1447 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-03-05 through 2026-03-06
Mon,Thu,Fri 14:50 Denver (DEN) 18:05 Chicago Midway (MDW)
Southwest Airlines WN 1447 Non-stop Boeing 737 MAX 8 (7M8) 2:15 Effective 2026-03-09 through 2026-04-06
Wed,Thu 16:45 Denver (DEN) 20:05 Chicago Midway (MDW)
Southwest Airlines WN 1454 Non-stop Boeing 737-700 (73W) 2:20 Valid until 2026-01-01
Mon 20:45 Denver (DEN) 00:05 Chicago Midway (MDW)
Southwest Airlines WN 1454 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-01-05
The flight arrives 1 day after departure.
Tue,Wed 13:40 Denver (DEN) 17:05 Chicago Midway (MDW)
Southwest Airlines WN 1475 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-04-07 through 2026-06-03
Mon-Fri 12:05 Denver (DEN) 15:25 Chicago Midway (MDW)
Southwest Airlines WN 1522 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 12:05 Denver (DEN) 15:25 Chicago Midway (MDW)
Southwest Airlines WN 1522 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-01-18 through 2026-01-23
Mon-Fri 12:05 Denver (DEN) 15:25 Chicago Midway (MDW)
Southwest Airlines WN 1522 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 12:05 Denver (DEN) 15:25 Chicago Midway (MDW)
Southwest Airlines WN 1522 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-08 through 2026-02-11
Tue,Wed 12:05 Denver (DEN) 15:25 Chicago Midway (MDW)
Southwest Airlines WN 1522 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-18 through 2026-03-04
Mon,Thu,Fri 16:10 Denver (DEN) 19:30 Chicago Midway (MDW)
Southwest Airlines WN 1524 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 16:10 Denver (DEN) 19:30 Chicago Midway (MDW)
Southwest Airlines WN 1524 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-02-20 through 2026-03-01
Sat 16:40 Denver (DEN) 20:00 Chicago Midway (MDW)
Southwest Airlines WN 1524 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-02-14 through 2026-02-28
Sat 13:00 Denver (DEN) 16:20 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-02-07
Sat 13:05 Denver (DEN) 16:25 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-01-10 through 2026-01-31
Thu,Fri,Sun 17:40 Denver (DEN) 21:05 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-11 through 2026-01-16
Mon,Sun 17:40 Denver (DEN) 21:05 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 17:40 Denver (DEN) 21:05 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-01 through 2026-02-06
Mon,Sun 17:40 Denver (DEN) 21:05 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 17:40 Denver (DEN) 21:05 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-02-17 through 2026-02-23
Mon 17:40 Denver (DEN) 21:05 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Operates only on 2026-03-02
Mon,Thu,Fri 18:15 Denver (DEN) 21:45 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 18:15 Denver (DEN) 21:45 Chicago Midway (MDW)
Southwest Airlines WN 1525 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-02-20 through 2026-03-01
Sun 08:20 Denver (DEN) 11:45 Chicago Midway (MDW)
Southwest Airlines WN 1560 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-09 through 2026-09-27
Tue,Wed 08:25 Denver (DEN) 11:50 Chicago Midway (MDW)
Southwest Airlines WN 1560 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 08:25 Denver (DEN) 11:50 Chicago Midway (MDW)
Southwest Airlines WN 1560 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-08-06 through 2026-09-28
Mon,Thu,Fri 13:50 Denver (DEN) 17:15 Chicago Midway (MDW)
Southwest Airlines WN 1561 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-06 through 2026-09-28
Sun 13:55 Denver (DEN) 17:25 Chicago Midway (MDW)
Southwest Airlines WN 1561 Non-stop Boeing 737 MAX 8 (7M8) 2:30 Effective 2026-08-09 through 2026-09-27
Sat 15:05 Denver (DEN) 18:25 Chicago Midway (MDW)
Southwest Airlines WN 1561 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-08 through 2026-09-26
Tue,Wed 16:45 Denver (DEN) 20:05 Chicago Midway (MDW)
Southwest Airlines WN 1562 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 16:55 Denver (DEN) 20:15 Chicago Midway (MDW)
Southwest Airlines WN 1562 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-06 through 2026-09-28
Sun 17:20 Denver (DEN) 20:45 Chicago Midway (MDW)
Southwest Airlines WN 1562 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-08-09 through 2026-09-27
Mon,Thu,Fri 18:30 Denver (DEN) 22:00 Chicago Midway (MDW)
Southwest Airlines WN 1563 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-08-06 through 2026-09-28
Sun 18:35 Denver (DEN) 22:00 Chicago Midway (MDW)
Southwest Airlines WN 1563 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-08-09 through 2026-09-27
Tue,Wed 19:25 Denver (DEN) 22:50 Chicago Midway (MDW)
Southwest Airlines WN 1563 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-08-04 through 2026-09-30
Tue,Wed 06:30 Denver (DEN) 09:50 Chicago Midway (MDW)
Southwest Airlines WN 1564 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-04 through 2026-09-30
Mon,Thu,Fri 20:25 Denver (DEN) 23:45 Chicago Midway (MDW)
Southwest Airlines WN 1564 Non-stop Boeing 737-800 (73H) 2:20 Effective 2026-08-06 through 2026-09-28
Sun 21:00 Denver (DEN) 00:25 Chicago Midway (MDW)
Southwest Airlines WN 1564 Non-stop Boeing 737-800 (73H) 2:25 Effective 2026-08-09 through 2026-09-27
The flight arrives 1 day after departure.
Sun 14:35 Denver (DEN) 17:55 Chicago Midway (MDW)
Southwest Airlines WN 1590 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-04-12 through 2026-05-17
Sun 14:35 Denver (DEN) 17:55 Chicago Midway (MDW)
Southwest Airlines WN 1590 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Operates only on 2026-05-31
Mon,Thu,Fri 17:35 Denver (DEN) 21:05 Chicago Midway (MDW)
Southwest Airlines WN 1590 Non-stop Boeing 737-800 (73H) 2:30 Effective 2026-04-09 through 2026-06-01
Sat 17:45 Denver (DEN) 21:20 Chicago Midway (MDW)
Southwest Airlines WN 1590 Non-stop Boeing 737 MAX 8 (7M8) 2:35 Effective 2026-04-11 through 2026-05-30
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All airlines flying from Denver (DEN) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Operates only on 2026-01-01
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-10 through 2026-04-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-03-07 through 2026-04-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-03-05 through 2026-03-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-03-09 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Valid until 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (73W)

Direct Flights:

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

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:

Effective 2026-01-06 through 2026-01-14
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-18 through 2026-01-23
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-26 through 2026-02-04
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-08 through 2026-02-11
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-18 through 2026-03-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

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:

Effective 2026-02-14 through 2026-02-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Operates only on 2026-02-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-10 through 2026-01-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-11 through 2026-01-16
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-01-19 through 2026-01-25
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-02-01 through 2026-02-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-02-09 through 2026-02-15
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-02-17 through 2026-02-23
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Operates only on 2026-03-02
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-02-12 through 2026-02-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-02-20 through 2026-03-01
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Effective 2026-04-12 through 2026-05-17
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Operates only on 2026-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-09 through 2026-06-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:30, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-04-11 through 2026-05-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:35, non-stop
Boeing 737 MAX 8 (7M8)
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  • 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.