Southwest Airlines
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United States
Midway International Airport
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United States
Pensacola Regional Airport
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Scan through all non-stop flights from Chicago to Pensacola. The full flight schedule below gives an overview of all non-stop flights from MDW to PNS, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Pensacola is a humid subtropical or warm-temperate destination, featuring hot, humid summers with temperatures typically around 30°C (86°F) and mild to cool winters. The region is known for consistent rainfall throughout the year, peaking in summer. The area is known for its vibrant urban energy, diverse landscapes, and numerous outdoor activities.
You can visit Pensacola any time of the year, but the best months to explore are from to and from to .
Currently, there is only one airline operating non-stop flights from Chicago MDW to Pensacola PNS, 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 MDW PNS flight schedule.
Flights from MDW to PNS are operated 4 times a week, with an average of 1 flight per day. Departure times vary between 07:45 - 16:55. The earliest flight departs at 07:45, the last flight departs at 16:55. 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 Chicago to Pensacola takes 2 hours and 15 minutes. The flight distance between Chicago and Pensacola is 781 miles (or 1,257 km).
There is 1 airport in Pensacola: Pensacola Regional Airport (PNS).
There are 4 flights per week flying from Chicago to Pensacola (as of March 2026).
2 hours and 15 minutes is the average flight time from Chicago to Pensacola.
The distance from Chicago to Pensacola is 781 miles (1,257 kilometers).
Southwest Airlines is the only airline flying nonstop from Chicago to Pensacola.
There are no alliances flying direct from Chicago to Pensacola at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Chicago to Pensacola:
The earliest flight departs at 07:45 from Chicago and arrives at 10:00 at Pensacola.
The latest flight departs at 16:55 from Chicago and arrives at 19:10 at Pensacola.
781 miles (1,257 km) · 2h 15m
08:00
10:20
Southwest Airlines
WN 2457
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:00
11:15
Southwest Airlines
WN 2457
Southwest Airlines
Boeing 757
Y
W
J
F
09:00
11:15
Southwest Airlines
WN 2457
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
12:15
14:25
Southwest Airlines
WN 2115
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:55
19:10
Southwest Airlines
WN 152
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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