Direct flights from Chicago to Montego Bay
- 1 flight a week
- Southwest Airlines
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When the nonstops leave
Typical weekly schedule · 1 flight per week · Updated 83d ago
Most leave in the morning.
Arrive the same day
10:10 AMSat
No nonstop leaves between noon and 6 PM.
No nonstop leaves after 6 PM.
Southwest Airlines
Frequently asked questions
Is there a direct flight from Chicago to Montego Bay?
Yes. 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). Schedule data from 29 July 2026.
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 times a week — 1 flight per week.
What days of the week are there direct flights from Chicago to Montego Bay?
Direct flights from Chicago to Montego Bay operate on Saturday.