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Flights from Chicago to Montego Bay – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

MDW to MBJ flights and routes map MDW to MBJ – All flight route options from Chicago Midway International, Illinois, USA to Sangster International, Jamaica. These flights are operated by 3 airlines. Fly non-stop with Southwest Airlines or choose from 5 different transit flights. The shortest flight time is 3 hours and 58 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA MDW Chicago Midway Chicago, IL, USA
Jamaica MBJ Sangster , Jamaica
MDW
Chicago Midway
USAChicago, IL, USA
Sangster
JamaicaMontego Bay, Jamaica
MBJ
1 direct route found »
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6 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 1 flight per day.

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3h 58m

Southwest Airlines
Non-stop with Southwest Airlines.
3h 58m
1 flight per day.
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1 stop route options with the same airline:

Duration

Via Saint Louis STL
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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5h 50m

Only sundays
Via Saint Louis STL
1 stop with Southwest Airlines.
5h 50m
0-1 flights per day.
Only sundays
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Via Orlando MCO
1 stop with Southwest Airlines. 1-2 flights per day.

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6h 45m

Via Orlando MCO
1 stop with Southwest Airlines.
6h 45m
1-2 flights per day.
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Via Atlanta ATL
1 stop with Delta Air Lines. 2-3 flights per day.

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7h 03m

Via Atlanta ATL
1 stop with Delta Air Lines.
7h 03m
2-3 flights per day.
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Via Baltimore BWI
1 stop with Southwest Airlines. 2 flights per day.

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7h 05m

Via Baltimore BWI
1 stop with Southwest Airlines.
7h 05m
2 flights per day.
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Via Fort Lauderdale FLL
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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7h 10m

Only saturdays
Via Fort Lauderdale FLL
1 stop with Southwest Airlines.
7h 10m
0-1 flights per day.
Only saturdays
SHOW SCHEDULE
Via Atlanta ATL
1 stop with Frontier Airlines. 0-1 flights per day.
Mon,Fri & Sat

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8h 20m

Mon,Fri & Sat
Via Atlanta ATL
1 stop with Frontier Airlines.
8h 20m
0-1 flights per day.
Mon,Fri & Sat
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Chicago to Montego Bay flights

With over 69 flights every week and 6 different airlines you have a wide range of options. You can fly non-stop to Montego Bay (MBJ) from Chicago (MDW) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Saint Louis, Orlando or any other of the 5 alternatives with connectiing airports.

Chicago to Montego Bay with Southwest Airlines

You can fly non-stop every weekday with flights departing at 08 or 09 in the morning. You can also catch a transit flight via Saint Louis or Orlando.

With Delta Air Lines

If you fly from Chicago with Delta Air Lines you will do a stopover in Atlanta, ATL before reaching Montego Bay. This flight trip will take 7 hours and 3 minutes and you can fly every weekday with departures at 06:00, 06:04 or 10:11. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Midway International Airport to Sangster International

The shortest flight time between MDW and MBJ is 3 hours and 58 minutes.

ViaTotal flight timeLayover timeDistance
Direct3h 58m-1719 miles (2766 km)
STL Saint Louis5h 50m1h 0m1847 miles (2972 km)
MCO Orlando6h 45m1h 55m1719 miles (2766 km)
ATL Atlanta7h 3m4h 46m1720 miles (2767 km)
BWI Baltimore7h 5m1h 45m2050 miles (3298 km)
FLL Fort Lauderdale7h 10m1h 10m1720 miles (2767 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.MDW-MBJ flight routesChicago to Montego Bay flight routes illustrated on a map.
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Chicago - Montego Bay route map and flight paths
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From Chicago to Jamaica

We have found another destination to Jamaica from Chicago Midway International as well.

From USA to Montego Bay

Below is a list of other cities in USA with flights to Montego Bay with either non-stop or connecting flights.

You can fly non-stop from Chicago (MDW) to Montego Bay (MBJ) with Southwest Airlines. The flight takes approximately 3 hours and 58 minutes. If you travel with a connecting flight instead, for example via Saint Louis, the total flight time will be 5 hours and 50 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Southwest Airlines and Delta Air Lines is also an option.

The flight time between Chicago Midway (MDW) and Sangster International (MBJ) is approximately 3 hours and 58 minutes. The distance between the two airports is 1720 miles (or 2767 kilometers).

Yes, you can fly non-stop to MBJ from MDW with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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