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Cheap flights from Chicago to Montego Bay

15 nonstop flights a week, 2 of them today. Operated by 3 airlines, about 4h 7m in the air, 1,716 mi (2,761 km). Tickets from $239, nonstop from $264.

Flights from Chicago to Montego Bay

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.

Prices by day: Chicago to Montego Bay

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

Filters

Best fares from Chicago to Montego Bay

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

Cheapest one-way $239 11 November 2026, with a connection Cheapest nonstop $264 11 November 2026, United Airlines Cheapest in the next 7 days $239 Today Cheapest month November 2026 tickets from $234

Chicago to Montego Bay at a glance

flight time, from 3h 55m to 4h 13m
4h 7m
straight-line distance
1,716 mi (2,761 km)
flights a week
15
flights today
2
first and last departure
08:05 - 09:45
lowest price, with a connection, 11 November
$239
lowest nonstop price
$264
airlines
3

Chicago to Montego Bay ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: November 2026, tickets from $234. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is December 2026: from $277. The average across months is $255.

Chicago to Montego Bay flight schedule

15 flights a week, 2 today, 16 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
WN 1042
Southwest Airlines
08:05 Chicago Midway International
13:00 Sangster International
3h 55m
Sat
Boeing 737
UA 1146
United Airlines
08:40 , terminal 1
13:48 Sangster International
4h 8m
Daily
Boeing 737
AA 3228
American Airlines
09:37 , terminal 3
14:49 Sangster International
4h 12m
Mon, Thu, Fri, Sun
Boeing 737-800
AA 3228
American Airlines
09:40 , terminal 3
14:52 Sangster International
4h 12m
Daily
Boeing 737-800
AA 3228
American Airlines
09:45 , terminal 3
14:57 Sangster International
4h 12m
Sat
Boeing 737-800

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 17 December.

FlightDepartsArrivesDurationDaysAircraft
AA 3228
American Airlines
09:19 , terminal 3
14:32 Sangster International
4h 13m
Seasonal
Boeing 737-800
AA 3228
American Airlines
09:00 , terminal 3
14:13 Sangster International
4h 13m
Seasonal
Boeing 737-800
AA 3228
American Airlines
10:05 , terminal 3
15:18 Sangster International
4h 13m
Seasonal
Boeing 737-800
WN 1042
Southwest Airlines
07:55 Chicago Midway International
12:50 Sangster International
3h 55m
Seasonal
Boeing 737
AA 1869
American Airlines
09:45 , terminal 3
14:52 Sangster International
4h 7m
Seasonal
Boeing 737-800
WN 1042
Southwest Airlines
08:10 Chicago Midway International
13:05 Sangster International
3h 55m
Seasonal
Boeing 737
UA 1146
United Airlines
08:42 , terminal 1
13:46 Sangster International
4h 4m
Seasonal
Boeing 737-800
AA 1881
American Airlines
08:05 , terminal 3
13:12 Sangster International
4h 7m
Seasonal
Boeing 737-800
WN 1042
Southwest Airlines
08:15 Chicago Midway International
12:15 Sangster International
4h
Seasonal
Boeing 737
AA 1881
American Airlines
10:21 , terminal 3
14:28 Sangster International
4h 7m
Seasonal
Boeing 737-800
AA 1138
American Airlines
09:45 , terminal 3
13:52 Sangster International
4h 7m
Seasonal
Boeing 737-800
AA 1662
American Airlines
10:21 , terminal 3
14:28 Sangster International
4h 7m
Seasonal
Boeing 737-800
AA 3228
American Airlines
08:05 , terminal 3
12:13 Sangster International
4h 8m
Seasonal
Boeing 737-800
WN 1042
Southwest Airlines
08:30 Chicago Midway International
12:25 Sangster International
3h 55m
Seasonal
Boeing 737
AA 3228
American Airlines
09:20 , terminal 3
13:30 Sangster International
4h 10m
Seasonal
Boeing 737-800
AA 3228
American Airlines
09:31 , terminal 3
13:31 Sangster International
4h
Seasonal
Boeing 737-800

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

Airlines flying Chicago to Montego Bay

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 Chicago to Montego Bay depart and land

Departure from Chicago

Chicago Midway International MDW

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

About the airport

Arrival in Montego Bay

Sangster International MBJ

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

About the airport

Frequently asked questions

How long is the flight from Chicago to Montego Bay?
A nonstop flight takes 4 hours 7 minutes on average, from 3h 55m to 4h 13m depending on the flight.
How far is Montego Bay from Chicago?
1,716 mi (2,761 km) in a straight line between the cities.
Which airlines fly nonstop from Chicago to Montego Bay?
American Airlines (7 a week), United Airlines (7 a week) and Southwest Airlines (1 a week).
How many flights a day are there from Chicago to Montego Bay?
2 flights today and 15 a week, about 2.1 a day on average.
When are the first and last flights from Chicago to Montego Bay?
The first departure is at 08:05 (WN1042), the last at 09:45 (AA3228). Local time.
What is the cheapest month to fly from Chicago to Montego Bay?
November 2026: tickets from $234. The most expensive is December 2026, from $277.
What is the cheapest upcoming date to fly from Chicago to Montego Bay?
11 November 2026 (Wednesday): from $239 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Chicago to Montego Bay?
United Airlines: nonstop tickets from $264 on 11 November by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Chicago and Montego Bay?
Montego Bay is 1 hour ahead of Chicago. Schedule times on this page are local to each airport.
Which Chicago airport do flights to Montego Bay leave from?
Chicago Midway International (1 a week).