Southwest Airlines
Did you mean flights from Chicago to Pensacola?
United States
Pensacola Regional Airport
Switch direction
United States
Midway International Airport
Click to show full flight schedule
Scan through all non-stop flights from Pensacola to Chicago. The full flight schedule below gives an overview of all non-stop flights from PNS 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 Pensacola PNS 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 PNS MDW flight schedule.
Flights from PNS to MDW are operated 4 times a week, with an average of 1 flight per day. Departure times vary between 10:20 - 18:10. The earliest flight departs at 10:20, the last flight departs at 18:10. 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 Pensacola to Chicago takes 2 hours and 20 minutes. The flight distance between Pensacola and Chicago is 781 miles (or 1,257 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 4 flights per week flying from Pensacola to Chicago (as of March 2026).
2 hours and 20 minutes is the average flight time from Pensacola to Chicago.
The distance from Pensacola to Chicago is 781 miles (1,257 kilometers).
Southwest Airlines is the only airline flying nonstop from Pensacola to Chicago.
There are no alliances flying direct from Pensacola to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Pensacola to Chicago:
The earliest flight departs at 10:20 from Pensacola and arrives at 12:35 at Chicago.
The latest flight departs at 18:10 from Pensacola and arrives at 20:25 at Chicago.
781 miles (1,257 km) · 2h 20m
10:20
12:35
Southwest Airlines
WN 4580
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:15
18:35
Southwest Airlines
WN 745
Southwest Airlines
Boeing 757
Y
W
J
F
17:20
19:35
Southwest Airlines
WN 4089
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:25
19:40
Southwest Airlines
WN 1929
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:10
20:25
Southwest Airlines
WN 4580
Southwest Airlines
Boeing 757
Y
W
J
F
Click to Check Prices
