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 46 minutes.
Choose airline
Schedules
Non-stop with Southwest Airlines
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Total flight time: 1 hour and 20 minutes
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Low-cost airline
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Chicago is a Southwest Airlines focus city (Operating base).
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22 flights per week
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Boeing 737MAX 8 PassengerBoeing 737-700 (winglets) Passenger/BBJ1Boeing 737-800 (winglets) Passenger/BBJ2
CLE
Direct
MDW
W8, Feb 17 - Feb 23
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN4191
06:35
06:55
07:05
06:55
06:35
06:00
06:35
WN2602
12:25
11:40
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11:40
12:25
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12:25
WN4165
18:35
18:25
19:00
18:25
18:35
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18:35
WN477
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19:30
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The timetable & schedule information was updated at 2025-01-15
Via Detroit with Delta Air Lines
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Total flight time: 2h 46m - 5h 17m.
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Sky Team Alliance
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20 flights per week
CLE
Via DTW
MDW
W8, Feb 17 - Feb 23
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
DL5432
DL3858
DL3858
06:25
06:25
06:25
06:25
06:25
06:25
06:25
DL3809
DL3867
DL3867
10:24
10:24
10:24
10:24
10:24
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10:24
DL3809
DL3869
DL3869
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12:00
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DL3821
DL3869
DL3869
14:15
14:15
14:15
14:15
14:15
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14:15
The timetable & schedule information was updated at 2025-01-15