Southwest Airlines
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Sarasota-Bradenton International Airport
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Midway International Airport
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Scan through all non-stop flights from Sarasota / Bradenton to Chicago. The full flight schedule below gives an overview of all non-stop flights from SRQ 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 Sarasota / Bradenton SRQ 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 SRQ MDW flight schedule.
Flights from SRQ to MDW are operated 11 times a week, with an average of 2 flights per day. Departure times vary between 05:15 - 18:55. The earliest flight departs at 05:15, the last flight departs at 18:55. 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 Sarasota / Bradenton to Chicago takes 2 hours and 40 minutes. The flight distance between Sarasota / Bradenton and Chicago is 1,036 miles (or 1,667 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 11 flights per week flying from Sarasota / Bradenton to Chicago (as of April 2026).
2 hours and 40 minutes is the average flight time from Sarasota / Bradenton to Chicago.
The distance from Sarasota / Bradenton to Chicago is 1,036 miles (1,667 kilometers).
Southwest Airlines is the only airline flying nonstop from Sarasota / Bradenton to Chicago.
There are no alliances flying direct from Sarasota / Bradenton to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Sarasota / Bradenton to Chicago:
The earliest flight departs at 05:15 from Sarasota / Bradenton and arrives at 06:55 at Chicago.
The latest flight departs at 18:55 from Sarasota / Bradenton and arrives at 20:45 at Chicago.
1,036 miles (1,667 km) · 2h 40m
06:35
08:25
Southwest Airlines
WN 2580
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:05
08:55
Southwest Airlines
WN 4424
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:15
09:05
Southwest Airlines
WN 2580
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:20
09:10
Southwest Airlines
WN 4425
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:05
14:00
Southwest Airlines
WN 442
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:40
14:40
Southwest Airlines
WN 3983
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
15:15
17:05
Southwest Airlines
WN 4425
Southwest Airlines
Boeing 757
Y
W
J
F
16:00
17:55
Southwest Airlines
WN 2707
Southwest Airlines
Boeing 757
Y
W
J
F
17:50
19:35
Southwest Airlines
WN 4425
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:25
20:20
Southwest Airlines
WN 858
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:45
20:35
Southwest Airlines
WN 858
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:50
20:35
Southwest Airlines
WN 4425
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:55
20:45
Southwest Airlines
WN 858
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
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