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

FLIGHT SCHEDULE
Direct Flights:
Tue,Wed 18:05 Chicago Midway (MDW) 20:20 Cleveland (CLE) Southwest Airlines WN 374 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-08-04 through 2026-09-30
Sun 18:10 Chicago Midway (MDW) 20:25 Cleveland (CLE) Southwest Airlines WN 374 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-08-09 through 2026-09-27
Thu,Fri,Sun 13:35 Chicago Midway (MDW) 15:45 Cleveland (CLE) Southwest Airlines WN 512 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-01-11 through 2026-01-16
Mon,Sun 13:35 Chicago Midway (MDW) 15:45 Cleveland (CLE) Southwest Airlines WN 512 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 13:35 Chicago Midway (MDW) 15:45 Cleveland (CLE) Southwest Airlines WN 512 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-02-01 through 2026-02-06
Mon,Sun 13:35 Chicago Midway (MDW) 15:45 Cleveland (CLE) Southwest Airlines WN 512 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 13:35 Chicago Midway (MDW) 15:45 Cleveland (CLE) Southwest Airlines WN 512 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-02-17 through 2026-02-23
Mon 13:35 Chicago Midway (MDW) 15:45 Cleveland (CLE) Southwest Airlines WN 512 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Operates only on 2026-03-02
Mon,Thu,Fri 08:05 Chicago Midway (MDW) 10:25 Cleveland (CLE) Southwest Airlines WN 646 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-08-06 through 2026-09-28
Tue,Wed 12:45 Chicago Midway (MDW) 14:55 Cleveland (CLE) Southwest Airlines WN 746 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-03-10 through 2026-04-01
Sun 12:55 Chicago Midway (MDW) 15:05 Cleveland (CLE) Southwest Airlines WN 746 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-03-08 through 2026-04-05
Tue,Wed 07:50 Chicago Midway (MDW) 10:05 Cleveland (CLE) Southwest Airlines WN 937 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-09 through 2026-07-29
Sun 08:55 Chicago Midway (MDW) 11:10 Cleveland (CLE) Southwest Airlines WN 1079 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Operates only on 2026-05-24
Tue,Wed 07:45 Chicago Midway (MDW) 09:55 Cleveland (CLE) Southwest Airlines WN 1372 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-04-07 through 2026-06-03
Wed,Thu 20:40 Chicago Midway (MDW) 22:55 Cleveland (CLE) Southwest Airlines WN 1454 Non-stop Boeing 737-700 (73W) 1:15 Valid until 2026-01-01
Mon,Thu,Fri 07:55 Chicago Midway (MDW) 10:10 Cleveland (CLE) Southwest Airlines WN 1712 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-04-09 through 2026-06-01
Mon,Thu,Fri 12:15 Chicago Midway (MDW) 14:25 Cleveland (CLE) Southwest Airlines WN 1813 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-06-04 through 2026-08-03
Sun 13:10 Chicago Midway (MDW) 15:20 Cleveland (CLE) Southwest Airlines WN 1813 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-06-07 through 2026-08-02
Sat 07:40 Chicago Midway (MDW) 09:50 Cleveland (CLE) Southwest Airlines WN 1932 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-04-11 through 2026-05-30
Tue,Wed 12:45 Chicago Midway (MDW) 15:00 Cleveland (CLE) Southwest Airlines WN 1932 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-04-07 through 2026-06-03
Mon,Thu,Fri 12:50 Chicago Midway (MDW) 15:05 Cleveland (CLE) Southwest Airlines WN 1932 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-04-09 through 2026-06-01
Sun 13:15 Chicago Midway (MDW) 15:30 Cleveland (CLE) Southwest Airlines WN 1932 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-04-12 through 2026-05-17
Sun 13:15 Chicago Midway (MDW) 15:30 Cleveland (CLE) Southwest Airlines WN 1932 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Operates only on 2026-05-31
Wed,Thu 10:05 Chicago Midway (MDW) 12:30 Cleveland (CLE) Southwest Airlines WN 1964 Non-stop Boeing 737-800 (73H) 1:25 Valid until 2026-01-01
Mon 13:30 Chicago Midway (MDW) 15:40 Cleveland (CLE) Southwest Airlines WN 1964 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Operates only on 2026-01-05
Tue,Wed,Sun 07:40 Chicago Midway (MDW) 09:50 Cleveland (CLE) Southwest Airlines WN 1997 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 11:45 Chicago Midway (MDW) 13:55 Cleveland (CLE) Southwest Airlines WN 1997 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-03-05 through 2026-04-06
Mon,Tue,Fri,Sun 09:35 Chicago Midway (MDW) 11:50 Cleveland (CLE) Southwest Airlines WN 2497 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Valid until 2026-01-04
Sat 12:45 Chicago Midway (MDW) 14:55 Cleveland (CLE) Southwest Airlines WN 2497 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Operates only on 2026-01-03
Tue,Wed 18:00 Chicago Midway (MDW) 20:10 Cleveland (CLE) Southwest Airlines WN 2536 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-03-10 through 2026-04-01
Mon,Thu,Fri 18:45 Chicago Midway (MDW) 20:55 Cleveland (CLE) Southwest Airlines WN 2536 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-03-05 through 2026-04-06
Sat 18:55 Chicago Midway (MDW) 21:05 Cleveland (CLE) Southwest Airlines WN 2536 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-03-07 through 2026-04-04
Sun 19:20 Chicago Midway (MDW) 21:35 Cleveland (CLE) Southwest Airlines WN 2536 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-03-08 through 2026-04-05
Sat 18:00 Chicago Midway (MDW) 20:10 Cleveland (CLE) Southwest Airlines WN 2587 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-06-06 through 2026-08-01
Sat 15:40 Chicago Midway (MDW) 17:50 Cleveland (CLE) Southwest Airlines WN 2612 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-04-11 through 2026-05-30
Tue,Wed 18:05 Chicago Midway (MDW) 20:20 Cleveland (CLE) Southwest Airlines WN 2612 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-04-07 through 2026-06-03
Sun 18:15 Chicago Midway (MDW) 20:25 Cleveland (CLE) Southwest Airlines WN 2612 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Operates only on 2026-05-24
Sun 18:45 Chicago Midway (MDW) 21:00 Cleveland (CLE) Southwest Airlines WN 2612 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-04-12 through 2026-05-17
Sun 18:45 Chicago Midway (MDW) 21:00 Cleveland (CLE) Southwest Airlines WN 2612 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Operates only on 2026-05-31
Mon,Thu,Fri 19:00 Chicago Midway (MDW) 21:15 Cleveland (CLE) Southwest Airlines WN 2612 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-04-09 through 2026-06-01
Fri,Sun 15:30 Chicago Midway (MDW) 17:40 Cleveland (CLE) Southwest Airlines WN 2662 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-01-02 through 2026-01-04
Mon,Thu,Fri 09:30 Chicago Midway (MDW) 11:40 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 09:30 Chicago Midway (MDW) 11:40 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-02-20 through 2026-03-01
Thu,Fri,Sun 09:50 Chicago Midway (MDW) 12:05 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-01-11 through 2026-01-16
Mon,Sun 09:50 Chicago Midway (MDW) 12:05 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 09:50 Chicago Midway (MDW) 12:05 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-01 through 2026-02-06
Mon,Sun 09:50 Chicago Midway (MDW) 12:05 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 09:50 Chicago Midway (MDW) 12:05 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-17 through 2026-02-23
Mon 09:50 Chicago Midway (MDW) 12:05 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Operates only on 2026-03-02
Sat 09:55 Chicago Midway (MDW) 12:10 Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-01-10 through 2026-02-07

1 2 3

A domestic route departing from the Chicago Midway airport (MDW) and arriving at Cleveland airport (CLE).
The flight distance is 306 miles, or 492 km.
The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-5 . 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 1:10 and 1:25.

Return (CLE-MDW) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN374

18:05

Chicago Midway (MDW)

20:20

Cleveland (CLE)

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN374

18:10

Chicago Midway (MDW)

20:25

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN512

13:35

Chicago Midway (MDW)

15:45

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN512

13:35

Chicago Midway (MDW)

15:45

Cleveland (CLE)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN512

13:35

Chicago Midway (MDW)

15:45

Cleveland (CLE)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN512

13:35

Chicago Midway (MDW)

15:45

Cleveland (CLE)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN512

13:35

Chicago Midway (MDW)

15:45

Cleveland (CLE)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN512

13:35

Chicago Midway (MDW)

15:45

Cleveland (CLE)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN646

08:05

Chicago Midway (MDW)

10:25

Cleveland (CLE)

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN746

12:45

Chicago Midway (MDW)

14:55

Cleveland (CLE)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN746

12:55

Chicago Midway (MDW)

15:05

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN937

07:50

Chicago Midway (MDW)

10:05

Cleveland (CLE)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1079

08:55

Chicago Midway (MDW)

11:10

Cleveland (CLE)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1372

07:45

Chicago Midway (MDW)

09:55

Cleveland (CLE)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN1454

20:40

Chicago Midway (MDW)

22:55

Cleveland (CLE)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737-700 (73W)

Direct Flights:

Southwest Airlines WN1712

07:55

Chicago Midway (MDW)

10:10

Cleveland (CLE)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN1813

12:15

Chicago Midway (MDW)

14:25

Cleveland (CLE)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1813

13:10

Chicago Midway (MDW)

15:20

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1932

07:40

Chicago Midway (MDW)

09:50

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1932

12:45

Chicago Midway (MDW)

15:00

Cleveland (CLE)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1932

12:50

Chicago Midway (MDW)

15:05

Cleveland (CLE)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1932

13:15

Chicago Midway (MDW)

15:30

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1932

13:15

Chicago Midway (MDW)

15:30

Cleveland (CLE)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1964

10:05

Chicago Midway (MDW)

12:30

Cleveland (CLE)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 1:25, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1964

13:30

Chicago Midway (MDW)

15:40

Cleveland (CLE)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1997

07:40

Chicago Midway (MDW)

09:50

Cleveland (CLE)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN1997

11:45

Chicago Midway (MDW)

13:55

Cleveland (CLE)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2497

09:35

Chicago Midway (MDW)

11:50

Cleveland (CLE)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2497

12:45

Chicago Midway (MDW)

14:55

Cleveland (CLE)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Direct Flights:

Southwest Airlines WN2536

18:00

Chicago Midway (MDW)

20:10

Cleveland (CLE)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2536

18:45

Chicago Midway (MDW)

20:55

Cleveland (CLE)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2536

18:55

Chicago Midway (MDW)

21:05

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2536

19:20

Chicago Midway (MDW)

21:35

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2587

18:00

Chicago Midway (MDW)

20:10

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:10, non-stop
Boeing 737-800 (73H)

Direct Flights:

Southwest Airlines WN2612

15:40

Chicago Midway (MDW)

17:50

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2612

18:05

Chicago Midway (MDW)

20:20

Cleveland (CLE)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2612

18:15

Chicago Midway (MDW)

20:25

Cleveland (CLE)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2612

18:45

Chicago Midway (MDW)

21:00

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2612

18:45

Chicago Midway (MDW)

21:00

Cleveland (CLE)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2612

19:00

Chicago Midway (MDW)

21:15

Cleveland (CLE)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2662

15:30

Chicago Midway (MDW)

17:40

Cleveland (CLE)

Effective 2026-01-02 through 2026-01-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2664

09:30

Chicago Midway (MDW)

11:40

Cleveland (CLE)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Direct Flights:

Southwest Airlines WN2664

09:30

Chicago Midway (MDW)

11:40

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

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

Direct Flights:

Southwest Airlines WN2664

09:50

Chicago Midway (MDW)

12:05

Cleveland (CLE)

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

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2664

09:50

Chicago Midway (MDW)

12:05

Cleveland (CLE)

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

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2664

09:50

Chicago Midway (MDW)

12:05

Cleveland (CLE)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2664

09:50

Chicago Midway (MDW)

12:05

Cleveland (CLE)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2664

09:50

Chicago Midway (MDW)

12:05

Cleveland (CLE)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2664

09:50

Chicago Midway (MDW)

12:05

Cleveland (CLE)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 1:15, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2664

09:55

Chicago Midway (MDW)

12:10

Cleveland (CLE)

Effective 2026-01-10 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 1:15, non-stop
Boeing 737 MAX 8 (7M8)

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A domestic route departing from the Chicago Midway airport (MDW) and arriving at Cleveland airport (CLE).
The flight distance is 306 miles, or 492 km.
The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-5 . 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 1:10 and 1:25.

Return (CLE-MDW) flights

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