Direct flights from San Juan to Chicago SJU → MDW
Southwest Airlines flies nonstop from San Juan (SJU) to Chicago (MDW), 3–4 times a week. The flight takes about 4h 45m and covers 2,059 miles (3,314 km). Arrivals run on time 72.9% at SJU and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule.
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Southwest Airlines
WN
Frequently asked questions
Is there a direct flight from San Juan to Chicago?
Yes, Southwest Airlines operates nonstop flights from San Juan (SJU) to Chicago (MDW).
Which airlines fly direct from San Juan to Chicago?
Southwest Airlines operates nonstop flights from San Juan to Chicago.
How long is the flight from San Juan to Chicago?
The nonstop flight from San Juan to Chicago takes ~4h 45m (approximately 3314 km).
How often do direct flights operate from San Juan to Chicago?
Nonstop flights from San Juan to Chicago operate 3–4×/week.
What is the on-time performance for flights from San Juan to Chicago?
Arrivals run on time 72.9% at SJU and 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule.
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