Direct flights from Chicago to Montego Bay
All flights from MDW to MBJ non-stop. There are direct flights from Chicago Midway International, Illinois, USA to Sangster International (MBJ), Jamaica every day of the week with Southwest Airlines. The flight distance is 1719 miles and the trip usually takes about 4 hours.
Airlines with non-stop routes:

Southwest Airlines

Frontier Airlines
No flights anymore
Flight schedule from Chicago to Montego Bay with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2025-04-22
Chicago to Montego Bay flight departures
Select a date to see all scheduled flight departures between MDW to MBJ.
MDW - MBJ information
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Distance1719 miles (2766 km)
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Flight time4 hours
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Airlines
Southwest
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AlliancesOne WorldSky TeamStar Alliance
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ClassesEconomyBusinessFirst Class
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Southwest AircraftBoeing 737 Passenger