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