Airlines with flights from Chicago to Cleveland

There are two airlines with scheduled flights between MDW and CLE. Southwest is the only airline with non-stop flights from Midway International Airport to Cleveland Hopkins International and the flight time is 1 hour and 15 minutes. You can also connect with Delta via Detroit with a flight time of 2 hours and 44 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 1 hour and 15 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 33 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
MDW
Direct
CLE
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN937
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07:50
07:50
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WN4088
07:55
13:40
13:40
07:55
07:55
07:50
08:00
WN1813
12:15
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12:15
12:15
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13:10
WN2774
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----
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13:35
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WN4506
17:25
15:45
15:45
17:25
17:25
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WN2587
----
----
----
----
----
18:00
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WN4153
19:35
18:15
18:15
19:35
19:35
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18:50
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - CLE

The timetable & schedule information was updated at 2026-04-21

Delta Air Lines

Via Detroit with Delta Air Lines

  • Total flight time: 2h 44m - 5h 00m.
  • Sky Team Alliance
  • 99 flights per week
MDW
 
Via DTW
 
CLE
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL4674
DL3559
09:17
09:17
09:17
09:17
09:17
09:17
09:17
DL4688
DL4954
13:16
13:16
13:16
13:16
13:16
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13:16
DL4688
DL3974
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----
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----
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13:16
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DL4690
DL3646
18:58
18:58
18:58
18:58
18:58
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18:58
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - CLE

The timetable & schedule information was updated at 2026-04-21

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Flight data on this page was last updated on 2026-06-02
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