Southwest Airlines
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Sangster International Airport
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Scan through all non-stop flights from Montego Bay to Chicago. The full flight schedule below gives an overview of all non-stop flights from MBJ to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
Currently, there is only one airline operating non-stop flights from Montego Bay MBJ to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their MBJ MDW flight schedule.
Flights from MBJ to MDW are operated once a week. Departure times vary between 11:35 - 14:30. The earliest flight departs at 11:35, the last flight departs at 14:30. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Montego Bay to Chicago takes 4 hours and 15 minutes. The flight distance between Montego Bay and Chicago is 1,709 miles (or 2,750 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (ORD).
There is 1 flight per week flying from Montego Bay to Chicago (as of April 2026).
4 hours and 15 minutes is the average flight time from Montego Bay to Chicago.
The distance from Montego Bay to Chicago is 1,709 miles (2,750 kilometers).
Southwest Airlines is the only airline flying nonstop from Montego Bay to Chicago.
There are no alliances flying direct from Montego Bay to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Montego Bay to Chicago:
The earliest flight departs at 11:35 from Montego Bay and arrives at 15:45 at Chicago.
The latest flight departs at 14:30 from Montego Bay and arrives at 18:35 at Chicago.
1,709 miles (2,750 km) · 4h 15m
11:35
15:45
Southwest Airlines
WN 1043
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
12:30
16:50
Southwest Airlines
WN 1043
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
14:20
18:35
Southwest Airlines
WN 1043
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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