Southwest Airlines
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Philadelphia International Airport
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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 34 times a week, with an average of 5 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 5 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 34 flights per week flying from Philadelphia to Chicago (as of July 2026).
2 hours and 5 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 07:45 at Chicago.
The latest flight departs at 20:55 from Philadelphia and arrives at 22:05 at Chicago.
666 miles (1,072 km) · 2h 5m
07:25
08:30
Southwest Airlines
WN 4154
Southwest Airlines
Boeing 737-700
Y
W
J
F
07:55
09:00
Southwest Airlines
WN 3531
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:00
09:05
Southwest Airlines
WN 4202
Southwest Airlines
Boeing 737-700
Y
W
J
F
08:10
09:20
Southwest Airlines
WN 4202
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
08:20
09:30
Southwest Airlines
WN 4202
Southwest Airlines
Boeing 737-700
Y
W
J
F
11:20
12:30
Southwest Airlines
WN 3224
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
11:25
12:35
Southwest Airlines
WN 3224
Southwest Airlines
Boeing 737-700
Y
W
J
F
11:25
12:35
Southwest Airlines
WN 606
Southwest Airlines
Boeing 737-700
Y
W
J
F
12:25
13:30
Southwest Airlines
WN 3224
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:50
13:50
Southwest Airlines
WN 4837
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:55
13:55
Southwest Airlines
WN 4837
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
13:00
14:00
Southwest Airlines
WN 1527
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:15
15:20
Southwest Airlines
WN 1456
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
14:50
15:55
Southwest Airlines
WN 4061
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
15:50
17:05
Southwest Airlines
WN 1622
Southwest Airlines
Boeing 737-700
Y
W
J
F
16:25
17:50
Southwest Airlines
WN 188
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
16:35
18:00
Southwest Airlines
WN 3112
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
17:20
18:30
Southwest Airlines
WN 2756
Southwest Airlines
Boeing 737-700
Y
W
J
F
18:05
19:15
Southwest Airlines
WN 2679
Southwest Airlines
Boeing 737-700
Y
W
J
F
18:40
20:05
Southwest Airlines
WN 3226
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
18:55
20:20
Southwest Airlines
WN 3226
Southwest Airlines
Boeing 737-700
Y
W
J
F
19:10
20:35
Southwest Airlines
WN 3226
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
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