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Cheap flights from Montego Bay to Chicago

15 nonstop flights a week, 2 of them today. Operated by 3 airlines, about 4h 42m in the air, 1,716 mi (2,761 km). Tickets from $237, nonstop from $283.

Flights from Montego Bay to Chicago

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

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Best fares from Montego Bay to Chicago

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $237 14 November 2026, with a connection Cheapest nonstop $283 14 November 2026, United Airlines Cheapest in the next 7 days $237 14 November, Sat Cheapest weekend departure $237 Sat, 14 November 2026 Cheapest month November 2026 tickets from $237

Montego Bay to Chicago at a glance

flight time, from 4h 5m to 4h 56m
4h 42m
straight-line distance
1,716 mi (2,761 km)
flights a week
15
flights today
2
first and last departure
14:25 - 15:57
lowest price, with a connection, 14 November
$237
lowest nonstop price
$283
airlines
3

Montego Bay to Chicago flight schedule

15 flights a week, 2 today, 24 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 1043
Southwest Airlines
14:25 Sangster International
17:35 Chicago Midway International
4h 10m
Sat
Boeing 737
UA 1160
United Airlines
14:54 Sangster International
18:20 , terminal 5
4h 26m
Daily
Boeing 737
AA 975
American Airlines
15:49 Sangster International
19:45 , terminal 5
4h 56m
Mon, Thu, Fri, Sun
Boeing 737-800
AA 975
American Airlines
15:56 Sangster International
19:46 , terminal 5
4h 50m
Daily
Boeing 737-800
AA 975
American Airlines
15:57 Sangster International
19:53 , terminal 5
4h 56m
Sat
Boeing 737-800

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 2 December.

FlightDepartsArrivesDurationDaysAircraft
AA 975
American Airlines
15:58 Sangster International
19:45 , terminal 5
4h 47m
Seasonal
Boeing 737-800
AA 975
American Airlines
15:59 Sangster International
19:46 , terminal 5
4h 47m
Seasonal
Boeing 737-800
AA 975
American Airlines
15:32 Sangster International
19:19 , terminal 5
4h 47m
Seasonal
Boeing 737-800
AA 975
American Airlines
15:13 Sangster International
18:55 , terminal 5
4h 42m
Seasonal
Boeing 737-800
AA 975
American Airlines
16:18 Sangster International
19:58 , terminal 5
4h 40m
Seasonal
Boeing 737-800
WN 1043
Southwest Airlines
13:25 Sangster International
16:30 Chicago Midway International
4h 5m
Seasonal
Boeing 737
AA 975
American Airlines
16:00 Sangster International
19:46 , terminal 5
4h 46m
Seasonal
Boeing 737-800
WN 1043
Southwest Airlines
14:05 Sangster International
17:15 Chicago Midway International
4h 10m
Seasonal
Boeing 737
UA 1160
United Airlines
14:48 Sangster International
18:16 , terminal 5
4h 28m
Seasonal
Boeing 737-800
AA 1138
American Airlines
14:14 Sangster International
18:00 , terminal 5
4h 46m
Seasonal
Boeing 737-800
WN 1043
Southwest Airlines
15:20 Sangster International
18:35 Chicago Midway International
4h 15m
Seasonal
Boeing 737
WN 1043
Southwest Airlines
12:45 Sangster International
17:00 Chicago Midway International
4h 15m
Seasonal
Boeing 737
UA 1160
United Airlines
13:48 Sangster International
18:16 , terminal 5
4h 28m
Seasonal
Boeing 737-800
AA 1138
American Airlines
15:00 Sangster International
19:46 , terminal 5
4h 46m
Seasonal
Boeing 737-800
WN 1043
Southwest Airlines
14:20 Sangster International
18:35 Chicago Midway International
4h 15m
Seasonal
Boeing 737
AA 975
American Airlines
15:36 Sangster International
20:22 , terminal 5
4h 46m
Seasonal
Boeing 737-800
UA 1160
United Airlines
13:52 Sangster International
18:15 , terminal 5
4h 23m
Seasonal
Boeing 737
AA 975
American Airlines
15:00 Sangster International
19:46 , terminal 5
4h 46m
Seasonal
Boeing 737-800
AA 975
American Airlines
13:15 Sangster International
17:55 , terminal 5
4h 40m
Seasonal
Boeing 737-800
WN 1043
Southwest Airlines
12:35 Sangster International
16:50 Chicago Midway International
4h 15m
Seasonal
Boeing 737
AA 975
American Airlines
14:30 Sangster International
19:15 , terminal 5
4h 45m
Seasonal
Boeing 737-800
AA 975
American Airlines
14:31 Sangster International
19:10 , terminal 5
4h 39m
Seasonal
Boeing 737-800
AA 975
American Airlines
14:36 Sangster International
19:27 , terminal 5
4h 51m
Seasonal
Boeing 737-800
AA 975
American Airlines
14:12 Sangster International
18:55 , terminal 5
4h 43m
Seasonal
Boeing 737-800

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Chicago is 1 hour behind Montego Bay. The search shows seat availability and the price for your date.

Airlines flying Montego Bay to Chicago

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

American Airlines7 a week United Airlines7 a week Southwest Airlines1 a week

Airports

Where flights from Montego Bay to Chicago depart and land

Departure from Montego Bay

Sangster International MBJ

15 flights a week, 2 mi (3 km) from the city centre

About the airport

Arrival in Chicago

Chicago Midway International MDW

1 flight a week, 9 mi (14 km) from the city centre

About the airport

When to visit Chicago

Weather by month

Best time to visit: May, June, July, August, September and October, +18° to +27° by day. In November it is +10° by day and +2° at night, with 7 rainy days.

Jan
0° −7° 10 days
Feb
+2° −6° 7 days
Mar
+9° 0° 12 days
Apr
+14° +5° 13 days
May
+19° +10° 11 days
Jun
+27° +17° 9 days
Jul
+27° +19° 12 days
Aug
+27° +19° 10 days
Sep
+24° +16° 7 days
Oct
+18° +10° 11 days
Nov
+10° +2° 7 days
Dec
+4° −3° 10 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Frequently asked questions

How long is the flight from Montego Bay to Chicago?
A nonstop flight takes 4 hours 42 minutes on average, from 4h 5m to 4h 56m depending on the flight.
How far is Chicago from Montego Bay?
1,716 mi (2,761 km) in a straight line between the cities.
Which airlines fly nonstop from Montego Bay to Chicago?
American Airlines (7 a week), United Airlines (7 a week) and Southwest Airlines (1 a week).
How many flights a day are there from Montego Bay to Chicago?
2 flights today and 15 a week, about 2.1 a day on average.
When are the first and last flights from Montego Bay to Chicago?
The first departure is at 14:25 (WN1043), the last at 15:57 (AA975). Local time.
What is the cheapest upcoming date to fly from Montego Bay to Chicago?
14 November 2026 (Saturday): from $237 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Montego Bay to Chicago?
United Airlines: nonstop tickets from $283 on 14 November by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Montego Bay and Chicago?
Chicago is 1 hour behind Montego Bay. Schedule times on this page are local to each airport.
Which Montego Bay airport do flights to Chicago leave from?
Sangster International (15 a week).