There are 4 ways to get from Chicago to Montego Bay by plane or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly from Chicago Midway International Airport
best- Fly from Chicago Midway International Airport (MDW) to Sangster International Airport (MBJ)MDW - MBJ
6h 26m$182–805Fly from Chicago O'Hare International Airport
- Fly from Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ)ORD - MBJ
6h 52m$222–435Train to South Bend, fly
- Take the train from Van Buren St. to South Bend Airport
- Fly from South Bend (SBN) to Sangster International Airport (MBJ)SBN - MBJ
10h 10m$233–1,014Train to General Mitchell International Airport, fly
- Take the train from Chicago Union Station to Milwaukee
- Fly from General Mitchell International Airport (MKE) to Sangster International Airport (MBJ)MKE - MBJ
10h 3m$305–1,321
Chicago Midway International Airport (MDW) to Sangster International Airport (MBJ) flights
Questions & Answers
The cheapest way to get from Chicago to Montego Bay is to fly which costs $220 - $440 and takes 6h 52m.
The fastest way to get from Chicago to Montego Bay is to fly which takes 6h 26m and costs $180 - $850.
The distance between Chicago and Montego Bay is 2769 km.
It takes approximately 6h 26m to get from Chicago to Montego Bay, including transfers.
Montego Bay is 1h ahead of Chicago. It is currently 9:51 AM in Chicago and 10:51 AM in Montego Bay.
There are 416+ hotels available in Montego Bay.
What companies run services between Chicago, IL, USA and Montego Bay, Jamaica?
Southwest Airlines, Delta, and Frontier Airlines fly from Chicago Midway International Airport (MDW) to Sangster International Airport (MBJ) 4 times a day.
Transport is disrupted due to the Russia-Ukraine war. Read more
- Website
- southwest.com
Flights from Chicago Midway International Airport to Sangster International Airport
- Ave. Duration
- 3h 55m
- When
- Saturday
- Estimated price
- $180–800
Flights from Chicago Midway International Airport to Sangster International Airport via Fort Lauderdale
- Ave. Duration
- 6h 5m
- When
- Saturday
- Estimated price
- $180–800
Flights from Chicago Midway International Airport to Sangster International Airport via Orlando
- Ave. Duration
- 7h 20m
- When
- Every day
- Estimated price
- $180–800
Flights from Chicago O'Hare International Airport to Sangster International Airport via Orlando
- Ave. Duration
- 5h 45m
- When
- Monday and Sunday
- Estimated price
- $150–700
Flights from General Mitchell International Airport to Sangster International Airport via Orlando
- Ave. Duration
- 6h 3m
- When
- Monday, Thursday, and Saturday
- Estimated price
- $280–1,200
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Sangster International Airport
- Ave. Duration
- 4h 7m
- When
- Every day
- Estimated price
- $150–700
Flights from Chicago O'Hare International Airport to Sangster International Airport via Miami
- Ave. Duration
- 6h 36m
- When
- Every day
- Estimated price
- $150–700
Flights from South Bend to Sangster International Airport via Charlotte
- Ave. Duration
- 6h 55m
- When
- Every day
- Estimated price
- $220–1,000
Flights from South Bend to Sangster International Airport via Dallas/Ft.Worth
- Ave. Duration
- 9h 54m
- When
- Thursday
- Estimated price
- $290–1,200
Flights from South Bend to Sangster International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 6h 12m
- When
- Every day
- Estimated price
- $230–1,000
Flights from General Mitchell International Airport to Sangster International Airport via Miami
- Ave. Duration
- 6h 42m
- When
- Saturday
- Estimated price
- $280–1,200
Flights from General Mitchell International Airport to Sangster International Airport via Charlotte
- Ave. Duration
- 8h 35m
- When
- Every day
- Estimated price
- $280–1,300
- Website
- delta.com
Flights from Chicago Midway International Airport to Sangster International Airport via Atlanta
- Ave. Duration
- 6h 31m
- When
- Every day
- Estimated price
- $180–800
Flights from Chicago O'Hare International Airport to Sangster International Airport via Atlanta
- Ave. Duration
- 6h 23m
- When
- Every day
- Estimated price
- $150–700
Flights from South Bend to Sangster International Airport via Atlanta
- Ave. Duration
- 6h 54m
- When
- Every day
- Estimated price
- $220–1,000
Flights from General Mitchell International Airport to Sangster International Airport via Atlanta
- Ave. Duration
- 6h 8m
- When
- Every day
- Estimated price
- $280–1,200
- Website
- flyfrontier.com
Flights from Chicago Midway International Airport to Sangster International Airport via Atlanta
- Ave. Duration
- 7h 12m
- When
- Monday
- Estimated price
- $180–800
Flights from Chicago O'Hare International Airport to Sangster International Airport via Atlanta
- Ave. Duration
- 7h 7m
- When
- Monday
- Estimated price
- $150–700
Flights from South Bend to Sangster International Airport via Atlanta
- Ave. Duration
- 8h 12m
- When
- Monday
- Estimated price
- $220–1,000
- Website
- united.com
Flights from Chicago O'Hare International Airport to Sangster International Airport
- Ave. Duration
- 4h 4m
- When
- Thursday to Saturday
- Estimated price
- $150–700
Flights from South Bend to Sangster International Airport via Chicago O'Hare International Airport
- Ave. Duration
- 6h 16m
- When
- Thursday to Saturday
- Estimated price
- $230–1,000
Flights from South Bend to Sangster International Airport via Washington Dulles
- Ave. Duration
- 6h 16m
- When
- Saturday
- Estimated price
- $240–1,100
- Website
- spirit.com
Flights from Chicago O'Hare International Airport to Sangster International Airport via Fort Lauderdale
- Ave. Duration
- 6h 10m
- When
- Tuesday, Thursday, and Sunday
- Estimated price
- $220–340
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from Van Buren St. to South Bend Airport
- Ave. Duration
- 1h 58m
- Frequency
- Every 2 hours
- Estimated price
- $13–15
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $13–15
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Milwaukee
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–45
- Website
- https://www.amtrak.com/home.html
Want to know more about travelling around Jamaica
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