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 25 minutes. You can also connect with Delta via Detroit with a flight time of 2 hours and 51 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 1 hour and 25 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 26 flights per week
  • Boeing 737-800 (winglets) Passenger/BBJ2
    Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
CLE
Direct
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1142
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08:45
08:45
08:50
08:50
08:55
08:55
WN4171
08:55
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WN1161
12:05
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WN1654
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12:50
12:50
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WN1354
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----
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13:45
WN2097
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----
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13:50
13:50
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WN4949
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16:35
16:00
WN1162
16:45
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WN491
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17:25
17:25
17:25
17:25
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WN175
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19:15
19:15
19:15
19:15
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WN1456
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----
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19:20
WN1163
20:10
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SHOW RETURN SCHEDULE
CHECK PRICES FOR CLE - MDW

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

Delta Air Lines

Via Detroit with Delta Air Lines

  • Total flight time: 2h 51m - 5h 18m.
  • Sky Team Alliance
  • 105 flights per week
CLE
 
Via DTW
 
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL3532
DL4684
06:40
06:40
06:40
06:40
06:40
06:40
06:40
DL3817
DL4688
08:18
08:18
08:18
08:18
08:18
08:18
08:18
DL3710
DL4688
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10:04
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DL5192
DL4688
10:24
10:24
10:24
10:24
10:24
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10:24
DL3559
DL4677
14:20
14:20
14:20
14:20
14:20
14:20
14:20
DL3581
DL4677
15:50
15:50
15:50
15:50
15:50
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15:50
DL5784
DL4677
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15:58
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SHOW RETURN SCHEDULE
CHECK PRICES FOR CLE - MDW

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

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Staying up-to-date with the airlines

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Flight data on this page was last updated on 2026-07-21
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