Airlines with flights from Tampa to Chicago

There are three airlines with scheduled flights between TPA and MDW. Southwest is the only airline with non-stop flights from Tampa International to Midway International Airport and the flight time is 2 hours and 45 minutes.

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Schedules

Southwest Airlines

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 45 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 38 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
TPA
Direct
MDW
 
Flight
Mon
Jun 15
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Jun 16
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Jun 17
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Jun 18
Fri
Jun 19
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Jun 20
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Jun 21
WN4031
05:20
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05:20
05:20
05:30
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WN1140
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06:55
06:55
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WN2412
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07:10
WN1156
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07:50
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WN2869
08:00
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08:00
08:00
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WN1655
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09:50
WN4033
10:45
10:40
10:40
10:45
10:45
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WN2762
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15:20
WN2587
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15:40
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WN4034
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18:30
18:30
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17:40
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WN3156
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18:10
WN3219
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20:20
WN4035
22:30
21:55
21:55
22:30
22:30
21:20
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SHOW RETURN SCHEDULE
CHECK PRICES FOR TPA - MDW

The timetable & schedule information was updated at 2026-04-22

Southwest Airlines

Via Columbus with Southwest Airlines

  • Total flight time: 4h 00m - 6h 15m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 53 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
TPA
 
Via CMH
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
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Jun 20
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Jun 21
WN4754
WN1503
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06:10
WN4754
WN1197
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06:25
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WN4754
WN4386
07:05
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07:05
07:05
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WN4754
WN1198
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07:35
07:35
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WN3502
WN481
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11:40
SHOW RETURN SCHEDULE
CHECK PRICES FOR TPA - MDW

The timetable & schedule information was updated at 2026-04-22

Southwest Airlines

Via Nashville with Southwest Airlines

  • Total flight time: 4h 05m - 8h 40m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 182 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
TPA
 
Via BNA
 
MDW
 
Flight
Mon
Jun 15
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Jun 16
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Jun 17
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Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4002
WN507
07:30
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07:30
07:30
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WN4003
WN2741
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08:10
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WN4002
WN1430
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09:40
09:40
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WN4002
WN1009
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09:40
WN4003
WN2241
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11:55
11:55
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WN4003
WN481
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11:55
WN294
WN4286
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13:45
13:45
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WN4004
WN2241
14:05
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14:05
14:05
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WN4004
WN478
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14:30
WN432
WN4277
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16:35
WN4005
WN4286
17:20
16:55
16:55
17:20
17:20
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WN4005
WN4277
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17:55
WN4006
WN578
20:45
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20:45
20:45
19:50
19:35
WN4314
WN578
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19:45
19:45
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SHOW RETURN SCHEDULE
CHECK PRICES FOR TPA - MDW

The timetable & schedule information was updated at 2026-04-22

Southwest Airlines

Via Atlanta with Southwest Airlines

  • Total flight time: 4h 05m - 6h 25m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 74 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
TPA
 
Via ATL
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
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Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN4987
WN2048
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07:50
WN3169
WN3903
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08:00
08:00
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WN4987
WN225
09:20
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09:20
09:20
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WN3521
WN103
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10:35
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WN3997
WN233
16:00
16:40
16:40
16:00
16:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR TPA - MDW

The timetable & schedule information was updated at 2026-04-22

Southwest Airlines

Via Saint Louis with Southwest Airlines

  • Total flight time: 4h 10m - 8h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 94 flights per week
  • Boeing 737MAX 8 Passenger
    Boeing 737-700 Passenger (Scimitar Winglets)
    Boeing 737-800 (winglets) Passenger/BBJ2
TPA
 
Via STL
 
MDW
 
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
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Jun 18
Fri
Jun 19
Sat
Jun 20
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Jun 21
WN4048
WN2570
05:50
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05:50
05:50
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05:55
WN4048
WN2665
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06:25
06:25
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WN4049
WN3344
10:15
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10:15
10:15
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WN3599
WN3957
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14:20
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WN4964
WN3957
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19:00
19:00
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SHOW RETURN SCHEDULE
CHECK PRICES FOR TPA - MDW

The timetable & schedule information was updated at 2026-04-22

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