Southwest Airlines
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Puerto Rico
Luis Muñoz Marín International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from San Juan to Chicago. The full flight schedule below gives an overview of all non-stop flights from SJU 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.
Currently, there is only one airline operating non-stop flights from San Juan SJU 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 SJU MDW flight schedule.
Flights from SJU to MDW are operated twice a week. Departure times vary between 12:55 - 16:25. The earliest flight departs at 12:55, the last flight departs at 16:25. 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 San Juan to Chicago takes 5 hours and 5 minutes. The flight distance between San Juan and Chicago is 2,057 miles (or 3,310 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (formerly Orchard Depot Fi (ORD).
There are 2 flights per week flying from San Juan to Chicago (as of May 2024).
5 hours and 5 minutes is the average flight time from San Juan to Chicago.
The distance from San Juan to Chicago is 2,057 miles (3,310 kilometers).
Southwest Airlines is the only airline flying nonstop from San Juan to Chicago.
There are no alliances flying direct from San Juan to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from San Juan to Chicago:
The earliest flight departs at 12:55 from San Juan and arrives at 16:55 at Chicago.
The latest flight departs at 16:25 from San Juan and arrives at 20:20 at Chicago.
2,057 miles (3,310 km) · 5h 5m
13:20
17:25
Southwest Airlines
WN 1839
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:00
18:05
Southwest Airlines
WN 406
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
14:10
18:15
Southwest Airlines
WN 1839
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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