Southwest Airlines
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United States
Tampa International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from Tampa to Chicago. The full flight schedule below gives an overview of all non-stop flights from TPA to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Tampa TPA to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their TPA MDW flight schedule.
Flights from TPA to MDW are operated 22 times a week, with an average of 3 flights per day. Departure times vary between 05:15 - 22:55. The earliest flight departs at 05:15, the last flight departs at 22:55. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Tampa to Chicago takes 2 hours and 45 minutes. The flight distance between Tampa and Chicago is 998 miles (or 1,606 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 22 flights per week flying from Tampa to Chicago (as of April 2026).
2 hours and 45 minutes is the average flight time from Tampa to Chicago.
The distance from Tampa to Chicago is 998 miles (1,606 kilometers).
Southwest Airlines is the only airline flying nonstop from Tampa to Chicago.
There are no alliances flying direct from Tampa to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Tampa to Chicago:
The earliest flight departs at 05:15 from Tampa and arrives at 06:55 at Chicago.
The latest flight departs at 22:55 from Tampa and arrives at 00:30 at Chicago.
998 miles (1,606 km) · 2h 45m
06:55
08:40
Southwest Airlines
WN 3701
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:00
08:50
Southwest Airlines
WN 3701
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:15
09:05
Southwest Airlines
WN 3701
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:00
10:45
Southwest Airlines
WN 2084
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
10:10
11:55
Southwest Airlines
WN 2084
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:30
12:15
Southwest Airlines
WN 2084
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:35
12:20
Southwest Airlines
WN 2084
Southwest Airlines
Boeing 757
Y
W
J
F
13:05
14:50
Southwest Airlines
WN 1035
Southwest Airlines
Boeing 757
Y
W
J
F
15:20
17:05
Southwest Airlines
WN 756
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
15:55
17:40
Southwest Airlines
WN 1972
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:20
18:10
Southwest Airlines
WN 756
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:00
19:45
Southwest Airlines
WN 1035
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:30
20:20
Southwest Airlines
WN 1035
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:40
20:25
Southwest Airlines
WN 1035
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
20:25
22:10
Southwest Airlines
WN 4561
Southwest Airlines
Boeing 757
Y
W
J
F
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