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.
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. Choose airline
Direct
Non-stop
2h 45min
Via Columbus
4h 0min
Via Nashville
4h 5min
Via Atlanta
4h 5min
Via Saint Louis
4h 10min
Via Atlanta
4h 11min
Via Louisville
4h 20min
Via Milwaukee
4h 20min
Via Raleigh/Durham
4h 25min
Via Pittsburgh
4h 25min
Via New Orleans
4h 35min
Via Kansas City
4h 55min
Via Washington
4h 55min
Via Indianapolis
4h 55min
Via Detroit
4h 56min
Via Atlanta
4h 59min
Via Baltimore
5h 5min
Via Fort Lauderdale
4h 55min
Starts 08/08
Via Birmingham
5h 40min
Starts 01/10
Via Memphis
4h 35min
Schedules
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).
-
30 flights per week
-
Boeing 737MAX 8 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
TPA
Direct
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4604
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----
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05:15
05:15
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WN4031
05:20
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----
----
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----
WN1963
----
----
----
07:05
07:05
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----
WN3943
----
07:35
07:35
11:00
11:00
07:25
11:00
WN802
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----
----
----
----
----
07:35
WN2869
08:00
----
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----
----
----
----
WN4033
10:45
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----
----
----
----
----
WN591
----
11:35
11:35
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----
13:00
----
WN5087
----
----
----
----
----
----
12:40
WN3944
----
17:35
17:35
17:25
17:25
18:00
17:35
WN4035
22:30
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The timetable & schedule information was updated at 2026-04-22
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 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
TPA
Via CMH
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN3533
WN1180
WN1180
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----
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06:55
06:55
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----
WN4754
WN4386
WN4386
07:05
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----
----
----
----
----
WN3201
WN4496
WN4496
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07:55
07:55
----
----
----
----
The timetable & schedule information was updated at 2026-04-22
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 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
TPA
Via BNA
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4002
WN507
WN507
07:30
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----
----
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----
WN2186
WN577
WN577
----
----
----
09:10
09:10
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----
WN3909
WN311
WN311
----
----
----
----
----
09:30
----
WN3908
WN573
WN573
----
10:05
10:05
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----
----
WN3908
WN684
WN684
----
----
----
----
----
----
10:10
WN3909
WN573
WN573
----
----
----
----
----
----
11:20
WN3909
WN575
WN575
----
12:00
12:00
13:40
13:40
----
----
WN2186
WN575
WN575
----
----
----
----
----
----
12:50
WN2186
WN4549
WN4549
----
----
----
----
----
14:05
----
WN4004
WN2241
WN2241
14:05
----
----
----
----
----
----
WN3981
WN860
WN860
----
----
----
----
----
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14:45
WN2186
WN576
WN576
----
15:40
15:40
----
----
----
----
WN4496
WN4549
WN4549
----
----
----
----
----
16:10
----
WN4005
WN4286
WN4286
17:20
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----
----
----
----
----
WN3910
WN4549
WN4549
----
----
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17:50
17:50
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----
WN2307
WN577
WN577
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----
----
----
----
----
18:00
WN4050
WN577
WN577
----
19:00
19:00
----
----
----
----
WN4006
WN578
WN578
20:45
----
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----
----
----
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The timetable & schedule information was updated at 2026-04-22
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 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
TPA
Via ATL
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN1969
WN2070
WN2070
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----
----
----
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06:20
WN4987
WN225
WN225
09:20
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----
----
----
----
WN4489
WN433
WN433
----
----
----
----
----
13:50
----
WN3997
WN233
WN233
16:00
----
----
----
----
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The timetable & schedule information was updated at 2026-04-22
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 PassengerBoeing 737-700 Passenger (Scimitar Winglets)Boeing 737-800 (winglets) Passenger/BBJ2
TPA
Via STL
MDW
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN4048
WN2570
WN2570
05:50
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----
----
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WN3958
WN3862
WN3862
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06:25
06:25
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----
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WN4049
WN3344
WN3344
10:15
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WN3400
WN3862
WN3862
----
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10:35
10:35
----
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WN746
WN2052
WN2052
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----
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12:35
----
WN2648
WN2742
WN2742
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----
----
----
----
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13:25
WN2905
WN3865
WN3865
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18:30
18:30
----
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The timetable & schedule information was updated at 2026-04-22
Via Atlanta with Delta
Via Atlanta with Frontier