All airlines flying from Cleveland Hopkins (CLE) to Midway, Chicago (MDW).

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FLIGHT SCHEDULE
Direct Flights:
Sat 18:40 Cleveland Hopkins (CLE) 19:00 Midway, Chicago (MDW)
Southwest Airlines WN 3862 Non-stop Boeing 737-800 (73H) 1:20 Effective 2025-06-07 through 2025-08-02
Mon,Thu,Fri,Sun 06:25 Cleveland Hopkins (CLE) 06:55 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 06:25 Cleveland Hopkins (CLE) 06:55 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Effective 2025-11-21 through 2025-11-28
Fri,Sun 06:25 Cleveland Hopkins (CLE) 06:55 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Effective 2025-12-07 through 2025-12-14
Thu 06:25 Cleveland Hopkins (CLE) 06:55 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Operates only on 2025-12-18
Mon 06:25 Cleveland Hopkins (CLE) 06:55 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Operates only on 2026-01-05
Tue,Wed,Sat 06:45 Cleveland Hopkins (CLE) 07:20 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2025-11-04 through 2025-11-15
Mon-Thu 06:45 Cleveland Hopkins (CLE) 07:20 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2025-11-17 through 2025-11-20
Mon-Sat 06:45 Cleveland Hopkins (CLE) 07:20 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2025-12-02 through 2025-12-11
Mon-Wed,Sat 06:45 Cleveland Hopkins (CLE) 07:20 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2025-12-13 through 2025-12-17
Wed,Thu 06:45 Cleveland Hopkins (CLE) 07:20 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2025-12-24 through 2026-01-01
Sun 08:05 Cleveland Hopkins (CLE) 08:30 Midway, Chicago (MDW)
Southwest Airlines WN 4277 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Operates only on 2025-11-30
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All airlines flying from Cleveland Hopkins (CLE) to Midway, Chicago (MDW).
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Select flight date:  Show Calendar
FLIGHT SCHEDULE
Direct Flights:

Effective 2025-06-07 through 2025-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 1:20, non-stop
Boeing 737-800 (73H)

Effective 2025-11-02 through 2025-11-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 1:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-21 through 2025-11-28
Mon
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 1:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-12-07 through 2025-12-14
Mon
-
Tue
-
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 1:30, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2025-12-18
Mon
-
Tue
-
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 1:30, non-stop
Boeing 737 MAX 8 (7M8)

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 1:30, non-stop
Boeing 737 MAX 8 (7M8)

Effective 2025-11-04 through 2025-11-15
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
Sun
-
Duration: 1:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-11-17 through 2025-11-20
Mon
Tue
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 1:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-02 through 2025-12-11
Mon
Tue
Wed
Thu
Fri
Sat
Sun
-
Duration: 1:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-13 through 2025-12-17
Mon
Tue
Wed
Thu
-
Fri
-
Sat
Sun
-
Duration: 1:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Effective 2025-12-24 through 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 1:35, non-stop
Boeing 737-700 (Scimitar Winglets)

Operates only on 2025-11-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 1:25, non-stop
Boeing 737-700 (Scimitar Winglets)
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  • A domestic route departing from the Cleveland Hopkins airport (CLE) and arriving at Midway, Chicago airport (MDW).
  • The flight distance is 306 miles, or 492 km.
  • The timezone of the departure airport is UTC-5 (plus 1h DST), and the timezone of the arrival airport is UTC-6 (plus 1h DST). Current time at the point of departure is 7:25pm, and 6:25pm at the point of arrival. There is a -1 hour time difference between the airports.
  • For direct flights, the flight time varies between 1:15 and 1:35.