Direct flights from Montego Bay to Chicago MBJ → MDW
Southwest Airlines flies nonstop from Montego Bay (MBJ) to Chicago (MDW), 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 24 July 2026.
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Southwest Airlines
WN
Departure Schedule typical week
Typical weekly schedule · 2 flights per week · Updated 37d ago
Southwest Airlines
Frequently asked questions
Is there a direct flight from Montego Bay to Chicago?
Yes, Southwest Airlines operates nonstop flights from Montego Bay (MBJ) to Chicago (MDW).
Which airlines fly direct from Montego Bay to Chicago?
Southwest Airlines operates nonstop flights from Montego Bay to Chicago.
How long is the flight from Montego Bay to Chicago?
The nonstop flight from Montego Bay to Chicago takes ~4h 2m (approximately 2752 km).
How often do direct flights operate from Montego Bay to Chicago?
Nonstop flights from Montego Bay to Chicago operate 1–2×/week — 2 flights per week.
What is the on-time performance for flights from Montego Bay to Chicago?
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 Montego Bay to Chicago?
Direct flights from Montego Bay to Chicago operate on Saturday and Sunday.
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