All airlines flying from Cleveland (CLE) to Chicago Midway (MDW).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Thu,Fri,Sun
20:00
Cleveland (CLE)
20:35
Chicago Midway (MDW) Southwest Airlines WN 1089 Non-stop Boeing 737-700 (Scimitar Winglets) 1:35 Effective 2026-02-20 through 2026-03-01 |
| Tue,Wed
08:45
Cleveland (CLE)
08:55
Chicago Midway (MDW) Southwest Airlines WN 1142 Non-stop Boeing 737 MAX 8 (7M8) 1:10 Effective 2026-08-04 through 2026-09-30 |
| Mon,Thu,Fri
08:50
Cleveland (CLE)
09:00
Chicago Midway (MDW) Southwest Airlines WN 1142 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-08-06 through 2026-09-28 |
| Sat
08:55
Cleveland (CLE)
09:05
Chicago Midway (MDW) Southwest Airlines WN 1142 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-08-08 through 2026-09-26 |
| Sun
09:10
Cleveland (CLE)
09:20
Chicago Midway (MDW) Southwest Airlines WN 1142 Non-stop Boeing 737-700 (Scimitar Winglets) 1:10 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
12:05
Cleveland (CLE)
12:20
Chicago Midway (MDW) Southwest Airlines WN 1161 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-06-04 through 2026-08-03 |
| Sat
12:30
Cleveland (CLE)
12:45
Chicago Midway (MDW) Southwest Airlines WN 1161 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-06-06 through 2026-08-01 |
| Tue,Wed
15:25
Cleveland (CLE)
15:40
Chicago Midway (MDW) Southwest Airlines WN 1162 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-06-09 through 2026-07-29 |
| Mon,Thu,Fri
16:45
Cleveland (CLE)
17:05
Chicago Midway (MDW) Southwest Airlines WN 1162 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-06-04 through 2026-08-03 |
| Sun
13:35
Cleveland (CLE)
13:50
Chicago Midway (MDW) Southwest Airlines WN 1163 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-06-07 through 2026-08-02 |
| Sat
18:50
Cleveland (CLE)
19:10
Chicago Midway (MDW) Southwest Airlines WN 1163 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-06-06 through 2026-08-01 |
| Tue,Wed
19:10
Cleveland (CLE)
19:30
Chicago Midway (MDW) Southwest Airlines WN 1163 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-06-09 through 2026-07-29 |
| Mon,Thu,Fri
20:10
Cleveland (CLE)
20:25
Chicago Midway (MDW) Southwest Airlines WN 1163 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
08:25
Cleveland (CLE)
08:40
Chicago Midway (MDW) Southwest Airlines WN 1257 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-09 through 2026-07-29 |
| Sat
09:05
Cleveland (CLE)
09:20
Chicago Midway (MDW) Southwest Airlines WN 1262 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-06 through 2026-08-01 |
| Sun
07:30
Cleveland (CLE)
07:50
Chicago Midway (MDW) Southwest Airlines WN 1292 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-04-12 through 2026-05-17 |
| Sun
07:30
Cleveland (CLE)
07:50
Chicago Midway (MDW) Southwest Airlines WN 1292 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Operates only on 2026-05-31 |
| Mon,Thu,Fri
15:45
Cleveland (CLE)
16:05
Chicago Midway (MDW) Southwest Airlines WN 1292 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-04-09 through 2026-06-01 |
| Sat
16:50
Cleveland (CLE)
17:10
Chicago Midway (MDW) Southwest Airlines WN 1292 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-04-11 through 2026-05-30 |
| Tue,Wed
18:45
Cleveland (CLE)
19:00
Chicago Midway (MDW) Southwest Airlines WN 1292 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-04-07 through 2026-06-03 |
| Tue,Wed
12:05
Cleveland (CLE)
12:20
Chicago Midway (MDW) Southwest Airlines WN 1306 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-06-09 through 2026-07-29 |
| Tue,Wed
12:50
Cleveland (CLE)
13:05
Chicago Midway (MDW) Southwest Airlines WN 1354 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-08-04 through 2026-09-30 |
| Sun
13:45
Cleveland (CLE)
14:00
Chicago Midway (MDW) Southwest Airlines WN 1354 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-08-09 through 2026-09-27 |
| Mon,Tue,Fri,Sun
06:30
Cleveland (CLE)
07:00
Chicago Midway (MDW) Southwest Airlines WN 1371 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Valid until 2026-01-04 |
| Sat
06:35
Cleveland (CLE)
07:05
Chicago Midway (MDW) Southwest Airlines WN 1371 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Valid until 2026-01-03 |
| Sat
08:50
Cleveland (CLE)
09:05
Chicago Midway (MDW) Southwest Airlines WN 1378 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-04-11 through 2026-05-30 |
| Mon,Thu,Fri
08:55
Cleveland (CLE)
09:10
Chicago Midway (MDW) Southwest Airlines WN 1378 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-04-09 through 2026-06-01 |
| Tue,Wed
09:00
Cleveland (CLE)
09:15
Chicago Midway (MDW) Southwest Airlines WN 1378 Non-stop Boeing 737-800 (73H) 1:15 Effective 2026-04-07 through 2026-06-03 |
| Sun
19:05
Cleveland (CLE)
19:25
Chicago Midway (MDW) Southwest Airlines WN 1378 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Operates only on 2026-05-24 |
| Sun
20:30
Cleveland (CLE)
20:50
Chicago Midway (MDW) Southwest Airlines WN 1378 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-04-12 through 2026-05-17 |
| Sun
20:30
Cleveland (CLE)
20:50
Chicago Midway (MDW) Southwest Airlines WN 1378 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Operates only on 2026-05-31 |
| Sun
11:05
Cleveland (CLE)
11:25
Chicago Midway (MDW) Southwest Airlines WN 1514 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-08 through 2026-04-05 |
| Mon
20:05
Cleveland (CLE)
20:35
Chicago Midway (MDW) Southwest Airlines WN 1640 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Operates only on 2026-01-05 |
| Sat
20:50
Cleveland (CLE)
21:15
Chicago Midway (MDW) Southwest Airlines WN 1640 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Operates only on 2026-01-03 |
| Fri,Sun
21:05
Cleveland (CLE)
21:25
Chicago Midway (MDW) Southwest Airlines WN 1640 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-01-02 through 2026-01-04 |
| Wed,Thu
13:10
Cleveland (CLE)
13:35
Chicago Midway (MDW) Southwest Airlines WN 1776 Non-stop Boeing 737-800 (73H) 1:25 Valid until 2026-01-01 |
| Sat
07:15
Cleveland (CLE)
07:45
Chicago Midway (MDW) Southwest Airlines WN 1875 Non-stop Boeing 737-700 (Scimitar Winglets) 1:30 Effective 2026-03-07 through 2026-04-04 |
| Mon,Thu,Fri
08:35
Cleveland (CLE)
09:00
Chicago Midway (MDW) Southwest Airlines WN 1875 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-03-05 through 2026-04-06 |
| Tue,Wed
08:40
Cleveland (CLE)
09:05
Chicago Midway (MDW) Southwest Airlines WN 1875 Non-stop Boeing 737-700 (Scimitar Winglets) 1:25 Effective 2026-03-10 through 2026-04-01 |
| Mon
15:30
Cleveland (CLE)
15:45
Chicago Midway (MDW) Southwest Airlines WN 1967 Non-stop Boeing 737-800 (73H) 1:15 Operates only on 2026-01-05 |
| Wed,Thu
16:35
Cleveland (CLE)
16:55
Chicago Midway (MDW) Southwest Airlines WN 1967 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Valid until 2026-01-01 |
| Mon,Thu,Fri
13:50
Cleveland (CLE)
14:05
Chicago Midway (MDW) Southwest Airlines WN 2097 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-08-06 through 2026-09-28 |
| Mon,Thu,Fri
19:50
Cleveland (CLE)
20:10
Chicago Midway (MDW) Southwest Airlines WN 2211 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-03-05 through 2026-04-06 |
| Fri,Sun
15:10
Cleveland (CLE)
15:30
Chicago Midway (MDW) Southwest Airlines WN 2409 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-01-02 through 2026-01-04 |
| Sat
20:00
Cleveland (CLE)
20:20
Chicago Midway (MDW) Southwest Airlines WN 2841 Non-stop Boeing 737-800 (73H) 1:20 Effective 2026-03-07 through 2026-04-04 |
| Sun
20:30
Cleveland (CLE)
20:50
Chicago Midway (MDW) Southwest Airlines WN 2841 Non-stop Boeing 737 MAX 8 (7M8) 1:20 Effective 2026-03-08 through 2026-04-05 |
| Mon,Thu,Fri
20:05
Cleveland (CLE)
20:25
Chicago Midway (MDW) Southwest Airlines WN 3731 Non-stop Boeing 737-700 (Scimitar Winglets) 1:20 Effective 2026-04-09 through 2026-06-01 |
| Sun
08:20
Cleveland (CLE)
08:35
Chicago Midway (MDW) Southwest Airlines WN 4171 Non-stop Boeing 737 MAX 8 (7M8) 1:15 Effective 2026-06-07 through 2026-08-02 |
| Mon,Thu,Fri
08:55
Cleveland (CLE)
09:10
Chicago Midway (MDW) Southwest Airlines WN 4171 Non-stop Boeing 737-700 (Scimitar Winglets) 1:15 Effective 2026-06-04 through 2026-08-03 |
| Mon
06:25
Cleveland (CLE)
06:55
Chicago Midway (MDW) Southwest Airlines WN 4277 Non-stop Boeing 737 MAX 8 (7M8) 1:30 Operates only on 2026-01-05 |
- 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.
