All airlines flying from Chicago Midway (MDW) to Cleveland (CLE).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sat
11:00
Chicago Midway (MDW)
13:10
Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-02-14 through 2026-02-28 |
| Tue,Wed
14:35
Chicago Midway (MDW)
16:45
Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-02-10 through 2026-02-11 |
| Tue,Wed
14:35
Chicago Midway (MDW)
16:45
Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-02-18 through 2026-03-04 |
| Mon-Fri
15:00
Chicago Midway (MDW)
17:10
Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
15:00
Chicago Midway (MDW)
17:10
Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
15:00
Chicago Midway (MDW)
17:10
Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-01-26 through 2026-02-04 |
| Sun
15:00
Chicago Midway (MDW)
17:10
Cleveland (CLE) Southwest Airlines WN 2664 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Operates only on 2026-02-08 |
| Mon,Thu,Fri
14:20
Chicago Midway (MDW)
16:30
Cleveland (CLE) Southwest Airlines WN 2665 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
14:20
Chicago Midway (MDW)
16:30
Cleveland (CLE) Southwest Airlines WN 2665 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-02-20 through 2026-03-01 |
| Sat
17:35
Chicago Midway (MDW)
19:50
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-01-10 through 2026-02-07 |
| Sat
18:00
Chicago Midway (MDW)
20:15
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-14 through 2026-02-28 |
| Thu,Fri,Sun
18:15
Chicago Midway (MDW)
20:30
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
18:15
Chicago Midway (MDW)
20:30
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
18:15
Chicago Midway (MDW)
20:30
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
18:15
Chicago Midway (MDW)
20:30
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
18:15
Chicago Midway (MDW)
20:30
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-17 through 2026-02-23 |
| Mon
18:15
Chicago Midway (MDW)
20:30
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Operates only on 2026-03-02 |
| Mon,Thu,Fri
19:20
Chicago Midway (MDW)
21:35
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
19:20
Chicago Midway (MDW)
21:35
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-20 through 2026-03-01 |
| Mon-Fri
19:55
Chicago Midway (MDW)
22:10
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
19:55
Chicago Midway (MDW)
22:10
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
19:55
Chicago Midway (MDW)
22:10
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
19:55
Chicago Midway (MDW)
22:10
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
19:55
Chicago Midway (MDW)
22:10
Cleveland (CLE) Southwest Airlines WN 2666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-02-18 through 2026-03-04 |
| Mon
19:10
Chicago Midway (MDW)
21:25
Cleveland (CLE) Southwest Airlines WN 2742 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Operates only on 2026-01-05 |
| Fri,Sun
19:50
Chicago Midway (MDW)
22:00
Cleveland (CLE) Southwest Airlines WN 2742 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-01-02 through 2026-01-04 |
| Sat
20:50
Chicago Midway (MDW)
23:05
Cleveland (CLE) Southwest Airlines WN 2742 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Operates only on 2026-01-03 |
| Sat
13:35
Chicago Midway (MDW)
15:45
Cleveland (CLE) Southwest Airlines WN 2774 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-06-06 through 2026-08-01 |
| Sun
07:45
Chicago Midway (MDW)
09:55
Cleveland (CLE) Southwest Airlines WN 3199 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-04-12 through 2026-05-17 |
| Sun
07:45
Chicago Midway (MDW)
09:55
Cleveland (CLE) Southwest Airlines WN 3199 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Operates only on 2026-05-31 |
| Mon
09:40
Chicago Midway (MDW)
11:55
Cleveland (CLE) Southwest Airlines WN 3454 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Operates only on 2026-01-05 |
| Wed,Thu
13:40
Chicago Midway (MDW)
15:50
Cleveland (CLE) Southwest Airlines WN 3454 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Valid until 2026-01-01 |
| Mon,Thu,Fri
13:00
Chicago Midway (MDW)
15:10
Cleveland (CLE) Southwest Airlines WN 3643 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-08-06 through 2026-09-28 |
| Sat,Sun
15:20
Chicago Midway (MDW)
17:30
Cleveland (CLE) Southwest Airlines WN 3643 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-08-08 through 2026-09-27 |
| Tue,Wed
16:15
Chicago Midway (MDW)
18:30
Cleveland (CLE) Southwest Airlines WN 3643 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-08-04 through 2026-09-30 |
| Tue,Wed
12:35
Chicago Midway (MDW)
14:45
Cleveland (CLE) Southwest Airlines WN 3666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-08-04 through 2026-09-30 |
| Sun
13:05
Chicago Midway (MDW)
15:15
Cleveland (CLE) Southwest Airlines WN 3666 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
16:25
Chicago Midway (MDW)
18:40
Cleveland (CLE) Southwest Airlines WN 3666 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-08-06 through 2026-09-28 |
| Mon,Thu,Fri
08:00
Chicago Midway (MDW)
10:15
Cleveland (CLE) Southwest Airlines WN 4008 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-03-05 through 2026-04-06 |
| Sat
08:00
Chicago Midway (MDW)
10:15
Cleveland (CLE) Southwest Airlines WN 4008 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-03-07 through 2026-04-04 |
| Sat
07:50
Chicago Midway (MDW)
10:05
Cleveland (CLE) Southwest Airlines WN 4088 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-06-06 through 2026-08-01 |
| Mon,Thu,Fri
07:55
Chicago Midway (MDW)
10:10
Cleveland (CLE) Southwest Airlines WN 4088 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-06-04 through 2026-08-03 |
| Sun
08:00
Chicago Midway (MDW)
10:15
Cleveland (CLE) Southwest Airlines WN 4088 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-06-07 through 2026-08-02 |
| Tue,Wed
13:40
Chicago Midway (MDW)
15:50
Cleveland (CLE) Southwest Airlines WN 4088 Non-stop Boeing 737-800 (73H) 1:10 Effective 2026-06-09 through 2026-07-29 |
| Tue,Wed
18:15
Chicago Midway (MDW)
20:25
Cleveland (CLE) Southwest Airlines WN 4153 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-06-09 through 2026-07-29 |
| Sun
18:50
Chicago Midway (MDW)
21:05
Cleveland (CLE) Southwest Airlines WN 4153 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
19:35
Chicago Midway (MDW)
21:50
Cleveland (CLE) Southwest Airlines WN 4153 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
15:45
Chicago Midway (MDW)
17:55
Cleveland (CLE) Southwest Airlines WN 4506 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-06-09 through 2026-07-29 |
| Mon,Thu,Fri
17:25
Chicago Midway (MDW)
19:35
Cleveland (CLE) Southwest Airlines WN 4506 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-06-04 through 2026-08-03 |
| Sat
07:40
Chicago Midway (MDW)
09:55
Cleveland (CLE) Southwest Airlines WN 4969 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-08-08 through 2026-09-26 |
- 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.
