Southwest Airlines
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Philadelphia International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from Philadelphia to Chicago. The full flight schedule below gives an overview of all non-stop flights from PHL 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 Philadelphia PHL 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 PHL MDW flight schedule.
Flights from PHL to MDW are operated 31 times a week, with an average of 4 flights per day. Departure times vary between 06:45 - 20:55. The earliest flight departs at 06:45, the last flight departs at 20:55. 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 Philadelphia to Chicago takes 2 hours and 10 minutes. The flight distance between Philadelphia and Chicago is 666 miles (or 1,072 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There are 31 flights per week flying from Philadelphia to Chicago (as of October 2026).
2 hours and 10 minutes is the average flight time from Philadelphia to Chicago.
The distance from Philadelphia to Chicago is 666 miles (1,072 kilometers).
Southwest Airlines is the only airline flying nonstop from Philadelphia to Chicago.
There are no alliances flying direct from Philadelphia to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Philadelphia to Chicago:
The earliest flight departs at 06:45 from Philadelphia and arrives at 07:50 at Chicago.
The latest flight departs at 20:55 from Philadelphia and arrives at 22:05 at Chicago.
666 miles (1,072 km) · 2h 10m
06:45
07:50
Southwest Airlines
WN 1426
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
06:55
08:00
Southwest Airlines
WN 1587
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:45
08:50
Southwest Airlines
WN 4580
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:55
09:00
Southwest Airlines
WN 4580
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
08:15
09:25
Southwest Airlines
WN 2235
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:15
11:25
Southwest Airlines
WN 2414
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:25
12:30
Southwest Airlines
WN 2177
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:30
12:35
Southwest Airlines
WN 3003
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:30
12:35
Southwest Airlines
WN 1848
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
11:45
12:50
Southwest Airlines
WN 3362
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
13:20
14:25
Southwest Airlines
WN 3340
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
13:55
15:00
Southwest Airlines
WN 4440
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
13:55
15:00
Southwest Airlines
WN 2987
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:45
15:50
Southwest Airlines
WN 3343
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:20
16:25
Southwest Airlines
WN 3433
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:45
17:50
Southwest Airlines
WN 2530
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:05
18:10
Southwest Airlines
WN 2961
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:30
18:35
Southwest Airlines
WN 1940
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:10
20:15
Southwest Airlines
WN 3363
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
19:40
20:45
Southwest Airlines
WN 3364
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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