Airlines with flights from Cleveland to Chicago
There are two airlines with scheduled flights between CLE and MDW. Southwest is the only airline with non-stop flights from Cleveland Hopkins International to Midway International Airport and the flight time is 1 hour and 20 minutes. You can also connect with Delta via Detroit with a flight time of 2 hours and 51 minutes.
There are two airlines with scheduled flights between CLE and MDW. Southwest is the only airline with non-stop flights from Cleveland Hopkins International to Midway International Airport and the flight time is 1 hour and 20 minutes. You can also connect with Delta via Detroit with a flight time of 2 hours and 51 minutes. Choose airline
Direct
Non-stop
1h 20min
Via Detroit
2h 51min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 1 hour and 20 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
24 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
CLE
Direct
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4171
08:55
----
----
08:55
08:55
----
08:20
WN1257
----
08:25
08:25
----
----
----
----
WN1262
----
----
----
----
----
09:05
----
WN1161
12:05
----
----
12:05
12:05
12:30
----
WN1306
----
12:05
12:05
----
----
----
----
WN1163
20:10
19:10
19:10
20:10
20:10
18:50
13:35
WN1162
16:45
15:25
15:25
16:45
16:45
----
----
WN267
----
----
----
----
----
----
20:10
The timetable & schedule information was updated at 2026-04-21
Via Detroit with Delta Air Lines
-
Total flight time: 2h 51m - 5h 18m.
-
Sky Team Alliance
-
105 flights per week
CLE
Via DTW
MDW
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL3532
DL4684
DL4684
06:30
06:30
06:30
06:30
06:30
06:30
06:30
DL3817
DL4688
DL4688
08:18
08:18
08:18
08:18
08:18
08:18
08:18
DL5192
DL4688
DL4688
10:26
10:26
10:26
10:26
10:26
10:24
10:26
DL3559
DL4677
DL4677
14:26
14:26
14:26
14:26
14:26
14:26
14:26
DL3581
DL4677
DL4677
16:00
16:00
16:00
16:00
16:00
16:00
16:00
The timetable & schedule information was updated at 2026-04-21
