All airlines flying from Colorado Springs (COS) to Chicago Midway (MDW).

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sun 10:05 Colorado Springs (COS) 13:25 Chicago Midway (MDW)
Southwest Airlines WN 264 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-08-09 through 2026-09-27
Sat 10:40 Colorado Springs (COS) 14:00 Chicago Midway (MDW)
Southwest Airlines WN 264 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-08 through 2026-09-26
Sun 09:25 Colorado Springs (COS) 12:50 Chicago Midway (MDW)
Southwest Airlines WN 472 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Effective 2026-06-07 through 2026-08-02
Tue,Wed 12:10 Colorado Springs (COS) 15:30 Chicago Midway (MDW)
Southwest Airlines WN 554 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 14:40 Colorado Springs (COS) 18:00 Chicago Midway (MDW)
Southwest Airlines WN 1228 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Effective 2026-06-04 through 2026-08-03
Sat 11:10 Colorado Springs (COS) 14:35 Chicago Midway (MDW)
Southwest Airlines WN 2082 Non-stop Boeing 737 MAX 8 (7M8) 2:25 Valid until 2026-01-03
Mon 15:10 Colorado Springs (COS) 18:30 Chicago Midway (MDW)
Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:20 Operates only on 2026-01-05
Fri,Sun 15:25 Colorado Springs (COS) 18:50 Chicago Midway (MDW)
Southwest Airlines WN 2082 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-01-02 through 2026-01-04
Sat 09:25 Colorado Springs (COS) 12:50 Chicago Midway (MDW)
Southwest Airlines WN 3130 Non-stop Boeing 737-700 (Scimitar Winglets) 2:25 Effective 2026-06-06 through 2026-08-01
Mon,Tue,Thu,Fri 13:15 Colorado Springs (COS) 16:35 Chicago Midway (MDW)
Southwest Airlines WN 3439 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-04 through 2026-09-29
Wed 13:15 Colorado Springs (COS) 16:35 Chicago Midway (MDW)
Southwest Airlines WN 3459 Non-stop Boeing 737 MAX 8 (7M8) 2:20 Effective 2026-08-05 through 2026-09-30
Non-Direct Flights:
Wed,Thu 05:15 Colorado Springs (COS) 11:15 Chicago Midway (MDW)
Southwest Airlines WN 265 1-stop Boeing 737 MAX 8 (7M8) 5:00 Valid until 2026-01-01
Sun 13:15 Colorado Springs (COS) 21:50 Chicago Midway (MDW)
Southwest Airlines WN 1223 2-stop Boeing 737-700 (Scimitar Winglets) 7:35 Effective 2026-06-07 through 2026-08-02


All airlines flying from Colorado Springs (COS) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
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 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

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:

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:

Valid until 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

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:

Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 2:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-08-04 through 2026-09-29
Mon
Tue
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-05 through 2026-09-30
Mon
-
Tue
-
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:20, non-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Valid until 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 5:00, 1-stop
Boeing 737 MAX 8 (7M8)

Non-Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 7:35, 2-stop
Boeing 737-700 (Scimitar Winglets)
  • A domestic route departing from the Colorado Springs airport (COS) and arriving at Chicago Midway airport (MDW).
  • The flight distance is 915 miles, or 1472 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 2:20 and 2:25.