All airlines flying from Cleveland (CLE) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Tue,Wed
19:15
Cleveland (CLE)
19:30
Chicago Midway (MDW) Southwest Airlines WN 175 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-08-04 through 2026-09-30 |
| Mon,Thu,Fri
19:15
Cleveland (CLE)
19:30
Chicago Midway (MDW) Southwest Airlines WN 175 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-08-06 through 2026-09-28 |
| Sun
19:20
Cleveland (CLE)
19:35
Chicago Midway (MDW) Southwest Airlines WN 175 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-08-09 through 2026-09-27 |
| Sun
20:10
Cleveland (CLE)
20:25
Chicago Midway (MDW) Southwest Airlines WN 267 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-07 through 2026-08-02 |
| Mon-Fri
06:15
Cleveland (CLE)
06:55
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737 MAX 8 (7M8) 1:40 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
06:15
Cleveland (CLE)
06:55
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737 MAX 8 (7M8) 1:40 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
06:15
Cleveland (CLE)
06:55
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737 MAX 8 (7M8) 1:40 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
06:15
Cleveland (CLE)
06:55
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737 MAX 8 (7M8) 1:40 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
06:15
Cleveland (CLE)
06:55
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737 MAX 8 (7M8) 1:40 Effective 2026-02-18 through 2026-03-04 |
| Mon,Thu,Fri
06:20
Cleveland (CLE)
06:55
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
06:20
Cleveland (CLE)
06:55
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-02-20 through 2026-03-01 |
| Sat
06:30
Cleveland (CLE)
07:05
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-02-14 through 2026-02-28 |
| Thu,Fri,Sun
06:35
Cleveland (CLE)
07:10
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
06:35
Cleveland (CLE)
07:10
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
06:35
Cleveland (CLE)
07:10
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
06:35
Cleveland (CLE)
07:10
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
06:35
Cleveland (CLE)
07:10
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-02-17 through 2026-02-23 |
| Mon
06:35
Cleveland (CLE)
07:10
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Operates only on 2026-03-02 |
| Sat
06:55
Cleveland (CLE)
07:30
Chicago Midway (MDW) Southwest Airlines WN 591 Non-stop Boeing 737-800 (73H) 1:35 Effective 2026-01-10 through 2026-02-07 |
| Tue,Wed
19:15
Cleveland (CLE)
19:40
Chicago Midway (MDW) Southwest Airlines WN 648 Non-stop Boeing 737 MAX 8 (7M8) 1:25 Effective 2026-03-10 through 2026-04-01 |
| Tue,Wed
14:45
Cleveland (CLE)
15:05
Chicago Midway (MDW) Southwest Airlines WN 675 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-04-07 through 2026-06-03 |
| Sun
16:10
Cleveland (CLE)
16:30
Chicago Midway (MDW) Southwest Airlines WN 675 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-04-12 through 2026-05-17 |
| Sun
16:10
Cleveland (CLE)
16:30
Chicago Midway (MDW) Southwest Airlines WN 675 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Operates only on 2026-05-31 |
| Thu,Fri,Sun
15:05
Cleveland (CLE)
15:30
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
15:05
Cleveland (CLE)
15:30
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
15:05
Cleveland (CLE)
15:30
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
15:05
Cleveland (CLE)
15:30
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
15:05
Cleveland (CLE)
15:30
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-02-17 through 2026-02-23 |
| Mon
15:05
Cleveland (CLE)
15:30
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Operates only on 2026-03-02 |
| Mon-Fri
16:25
Cleveland (CLE)
16:50
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737 MAX 8 (7M8) 1:25 Effective 2026-01-06 through 2026-01-14 |
| Tue-Fri,Sun
16:25
Cleveland (CLE)
16:50
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737 MAX 8 (7M8) 1:25 Effective 2026-01-18 through 2026-01-23 |
| Mon-Fri
16:25
Cleveland (CLE)
16:50
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737 MAX 8 (7M8) 1:25 Effective 2026-01-26 through 2026-02-04 |
| Tue,Wed,Sun
16:25
Cleveland (CLE)
16:50
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737 MAX 8 (7M8) 1:25 Effective 2026-02-08 through 2026-02-11 |
| Tue,Wed
16:25
Cleveland (CLE)
16:50
Chicago Midway (MDW) Southwest Airlines WN 762 Non-stop Boeing 737 MAX 8 (7M8) 1:25 Effective 2026-02-18 through 2026-03-04 |
| Mon,Thu,Fri
14:30
Cleveland (CLE)
14:50
Chicago Midway (MDW) Southwest Airlines WN 878 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
14:40
Cleveland (CLE)
15:00
Chicago Midway (MDW) Southwest Airlines WN 878 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-03-10 through 2026-04-01 |
| Sun
09:40
Cleveland (CLE)
09:55
Chicago Midway (MDW) Southwest Airlines WN 1021 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Operates only on 2026-05-24 |
| Sun
07:55
Cleveland (CLE)
08:20
Chicago Midway (MDW) Southwest Airlines WN 1086 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-03-08 through 2026-04-05 |
| Mon,Thu,Fri
12:15
Cleveland (CLE)
12:35
Chicago Midway (MDW) Southwest Airlines WN 1088 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-02-12 through 2026-02-16 |
| Thu,Fri,Sun
12:15
Cleveland (CLE)
12:35
Chicago Midway (MDW) Southwest Airlines WN 1088 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-02-20 through 2026-03-01 |
| Sat
18:10
Cleveland (CLE)
18:35
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-01-10 through 2026-02-07 |
| Thu,Fri,Sun
19:05
Cleveland (CLE)
19:40
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737 MAX 8 (7M8) 1:35 Effective 2026-01-11 through 2026-01-16 |
| Mon,Sun
19:05
Cleveland (CLE)
19:40
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737 MAX 8 (7M8) 1:35 Effective 2026-01-19 through 2026-01-25 |
| Thu,Fri,Sun
19:05
Cleveland (CLE)
19:40
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737 MAX 8 (7M8) 1:35 Effective 2026-02-01 through 2026-02-06 |
| Mon,Sun
19:05
Cleveland (CLE)
19:40
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737 MAX 8 (7M8) 1:35 Effective 2026-02-09 through 2026-02-15 |
| Mon,Tue,Thu
19:05
Cleveland (CLE)
19:40
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737 MAX 8 (7M8) 1:35 Effective 2026-02-17 through 2026-02-23 |
| Mon
19:05
Cleveland (CLE)
19:40
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737 MAX 8 (7M8) 1:35 Operates only on 2026-03-02 |
| Sat
19:15
Cleveland (CLE)
19:50
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Operates only on 2026-02-14 |
| Sat
19:15
Cleveland (CLE)
19:50
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737 MAX 8 (7M8) 1:35 Effective 2026-02-21 through 2026-02-28 |
| Mon,Thu,Fri
20:00
Cleveland (CLE)
20:35
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-02-12 through 2026-02-16 |
- A domestic route departing from the Cleveland airport (CLE) and arriving at Chicago Midway airport (MDW).
- The flight distance is 306 miles, or 492 km.
- The timezone of the departure airport is UTC-5 , 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 1:10 and 1:40.
