Direct flights from Chicago to Montego Bay MDW → MBJ
Southwest Airlines flies nonstop from Chicago (MDW) to Montego Bay (MBJ), 1–2 times a week. The flight takes about 4h 2m and covers 1,710 miles (2,752 km). Arrivals run on time 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule. Schedule data from 29 July 2026.
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Southwest Airlines
WN
Departure Schedule typical week
Typical weekly schedule · 1 flight per week · Updated 33d ago
Southwest Airlines
Frequently asked questions
Is there a direct flight from Chicago to Montego Bay?
Yes, Southwest Airlines operates nonstop flights from Chicago (MDW) to Montego Bay (MBJ).
Which airlines fly direct from Chicago to Montego Bay?
Southwest Airlines operates nonstop flights from Chicago to Montego Bay.
How long is the flight from Chicago to Montego Bay?
The nonstop flight from Chicago to Montego Bay takes ~4h 2m (approximately 2752 km).
How often do direct flights operate from Chicago to Montego Bay?
Nonstop flights from Chicago to Montego Bay operate 1–2×/week — 1 flight per week.
What is the on-time performance for flights from Chicago to Montego Bay?
Arrivals run on time 72.8% at MDW — BTS data for the last three months, counting arrivals within 15 minutes of schedule.
What days of the week are there direct flights from Chicago to Montego Bay?
Direct flights from Chicago to Montego Bay operate on Saturday.
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