All airlines flying from Kansas City (MCI) to Chicago Midway (MDW).

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sat 12:40 Kansas City (MCI) 14:05 Chicago Midway (MDW)
Southwest Airlines WN 4829 Non-stop Boeing 737 MAX 8 (7M8) 1:25 Effective 2026-08-08 through 2026-09-26
Sun 08:45 Kansas City (MCI) 10:10 Chicago Midway (MDW)
Southwest Airlines WN 5033 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-08-09 through 2026-09-27
Wed 14:00 Kansas City (MCI) 15:25 Chicago Midway (MDW)
Southwest Airlines WN 5116 Non-stop Boeing 737 MAX 8 (7M8) 1:25 Effective 2026-08-05 through 2026-09-30
Non-Direct Flights:
Tue,Wed 14:05 Kansas City (MCI) 17:00 Chicago Midway (MDW)
Southwest Airlines WN 2953 1-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-06-09 through 2026-07-29
Sun 14:35 Kansas City (MCI) 17:30 Chicago Midway (MDW)
Southwest Airlines WN 3326 1-stop Boeing 737-700 (Scimitar Winglets) 2:55 Effective 2026-03-08 through 2026-04-05
Tue,Wed 14:10 Kansas City (MCI) 17:10 Chicago Midway (MDW)
Southwest Airlines WN 3583 1-stop Boeing 737-700 (Scimitar Winglets) 3:00 Effective 2026-04-07 through 2026-06-03
Thu,Fri,Sun 10:10 Kansas City (MCI) 19:35 Chicago Midway (MDW)
Southwest Airlines WN 4569 3-stop Boeing 737-700 (Scimitar Winglets) 9:25 Effective 2026-01-11 through 2026-01-16
Mon,Sun 10:10 Kansas City (MCI) 19:35 Chicago Midway (MDW)
Southwest Airlines WN 4569 3-stop Boeing 737-700 (Scimitar Winglets) 9:25 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 10:10 Kansas City (MCI) 19:35 Chicago Midway (MDW)
Southwest Airlines WN 4569 3-stop Boeing 737-700 (Scimitar Winglets) 9:25 Effective 2026-02-01 through 2026-02-06
Mon,Sun 10:10 Kansas City (MCI) 19:35 Chicago Midway (MDW)
Southwest Airlines WN 4569 3-stop Boeing 737-700 (Scimitar Winglets) 9:25 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 10:10 Kansas City (MCI) 19:35 Chicago Midway (MDW)
Southwest Airlines WN 4569 3-stop Boeing 737-700 (Scimitar Winglets) 9:25 Effective 2026-02-17 through 2026-02-23
Mon 10:10 Kansas City (MCI) 19:35 Chicago Midway (MDW)
Southwest Airlines WN 4569 3-stop Boeing 737-700 (Scimitar Winglets) 9:25 Operates only on 2026-03-02
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All airlines flying from Kansas City (MCI) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Southwest Airlines WN4829
12:40
Kansas City (MCI)

14:05
Chicago Midway (MDW)
Effective 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 1:25, non-stop
Boeing 737 MAX 8 (7M8)
Direct Flights:
Southwest Airlines WN5033
08:45
Kansas City (MCI)

10:10
Chicago Midway (MDW)
Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:25, non-stop
Boeing 737-700 (Scimitar Winglets)
Direct Flights:
Southwest Airlines WN5116
14:00
Kansas City (MCI)

15:25
Chicago Midway (MDW)
Effective 2026-08-05 through 2026-09-30
Mon
-
Tue
-
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:25, non-stop
Boeing 737 MAX 8 (7M8)
Non-Direct Flights:
Southwest Airlines WN2953
14:05
Kansas City (MCI)

17:00
Chicago Midway (MDW)
Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 2:55, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN3326
14:35
Kansas City (MCI)

17:30
Chicago Midway (MDW)
Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 2:55, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN3583
14:10
Kansas City (MCI)

17:10
Chicago Midway (MDW)
Effective 2026-04-07 through 2026-06-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:00, 1-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4569
10:10
Kansas City (MCI)

19:35
Chicago Midway (MDW)
Effective 2026-01-11 through 2026-01-16
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 9:25, 3-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4569
10:10
Kansas City (MCI)

19:35
Chicago Midway (MDW)
Effective 2026-01-19 through 2026-01-25
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 9:25, 3-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4569
10:10
Kansas City (MCI)

19:35
Chicago Midway (MDW)
Effective 2026-02-01 through 2026-02-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 9:25, 3-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4569
10:10
Kansas City (MCI)

19:35
Chicago Midway (MDW)
Effective 2026-02-09 through 2026-02-15
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 9:25, 3-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4569
10:10
Kansas City (MCI)

19:35
Chicago Midway (MDW)
Effective 2026-02-17 through 2026-02-23
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 9:25, 3-stop
Boeing 737-700 (Scimitar Winglets)
Non-Direct Flights:
Southwest Airlines WN4569
10:10
Kansas City (MCI)

19:35
Chicago Midway (MDW)
Operates only on 2026-03-02
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 9:25, 3-stop
Boeing 737-700 (Scimitar Winglets)
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  • A domestic route departing from the Kansas City airport (MCI) and arriving at Chicago Midway airport (MDW).
  • The flight distance is 404 miles, or 651 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 1:20 and 1:35.
Return (MDW-MCI) flights
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