Nonstop flights from Chicago to Montego Bay
2 airlines fly from 2 Chicago airports (ORD and MDW) to Montego Bay (MBJ).
Routes
2 airport pairs- ORD to MBJChicago O'Hare to Sangster6 a week
- MDW to MBJChicago Midway to Sangster1 a week
When they leave
Chicago time8:05a9:00aFirst departure 8:05 AM, last 9:00 AM
Two in the morning, 8:05 AM to 9:00 AM.
Every flight
Earliest first
Schedules last checked Sep 19, 2026. Times are local.
Flying from Chicago to Montego Bay
American Airlines flies most often, 6 times a week on the Boeing 737-800. Southwest Airlines flies on Saturdays with the Boeing 737 MAX 8.
Flights run every day except Fridays, up to 2 a day. The first arrival in Montego Bay is at 1:00 PM and the last at 1:12 PM.
ORD to MBJ is the busiest airport pair, with 6 flights a week, then MDW to MBJ with 1.
On ORD to MBJ, American Airlines is back on Oct 10. On MDW to MBJ, Southwest Airlines starts on Nov 21.
Flying back, Montego Bay to Chicago has 7 nonstop flights a week.
Return flights
Find the cheapest day to fly from Chicago to Montego Bay.
Schedules as of Oct 9, 2026.