Airlines with flights from Pittsburgh to Chicago

There are two airlines with scheduled flights between PIT and MDW. Southwest is the only airline with non-stop flights from Pittsburgh Airport to Midway International Airport and the flight time is 1 hour and 30 minutes. You can also connect with Delta via Detroit with a flight time of 3 hours and 3 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 1 hour and 30 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 20 flights per week
  • Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737MAX 8 Passenger
    Boeing 737-800 (winglets) Passenger/BBJ2
PIT
Direct
MDW
 
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4810
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08:55
08:55
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08:05
WN2385
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14:00
14:00
08:40
08:40
08:40
17:15
WN3378
08:45
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WN3361
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11:45
WN2278
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14:45
14:45
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WN4707
15:50
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WN4179
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16:40
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WN3308
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18:55
18:55
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18:50
WN1271
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----
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19:30
19:30
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WN4073
20:15
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SHOW RETURN SCHEDULE
CHECK PRICES FOR PIT - MDW

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

Delta Air Lines

Via Detroit with Delta Air Lines

  • Total flight time: 3h 03m - 5h 32m.
  • Sky Team Alliance
  • 73 flights per week
PIT
 
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
DL5319
DL4684
06:20
06:20
06:20
06:20
06:20
06:20
06:20
DL5607
DL4688
10:26
10:26
10:26
10:26
10:26
10:26
10:26
SHOW RETURN SCHEDULE
CHECK PRICES FOR PIT - 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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