There are 3 ways to get from Montego Bay to Chicago 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 to Chicago Midway International Airport
best- Fly from Sangster International Airport (MBJ) to Chicago Midway International Airport (MDW)plane MBJ - MDW
4h 51m$255–1,114Fly to Chicago O'Hare International Airport
cheapest- Fly from Sangster International Airport (MBJ) to Chicago O'Hare International Airport (ORD)plane MBJ - ORD
5h 13m$181–785Fly to South Bend, train
- Fly from Sangster International Airport (MBJ) to South Bend (SBN)plane MBJ - SBN
- Take the train from South Bend Airport to Van Buren St.train
8h 36m$241–1,013
Sangster International Airport (MBJ) to Chicago Midway International Airport (MDW) flights
Comparing Your Travel Options
The cheapest way to get from Montego Bay to Chicago is to fly which costs $180 - $800 and takes 5h 13m.
The fastest way to get from Montego Bay to Chicago is to fly which takes 4h 51m and costs $250 - $1,200.
The distance between Montego Bay and Chicago is 1731 miles.
It takes approximately 4h 51m to get from Montego Bay to Chicago, including transfers.
Chicago is 1h behind Montego Bay. It is currently 10:14 PM in Montego Bay and 9:14 PM in Chicago.
There are 1315+ hotels available in Chicago.
What companies run services between Montego Bay, Jamaica and Chicago, IL, USA?
Southwest Airlines, Frontier Airlines, and Delta fly from Sangster International Airport (MBJ) to Chicago Midway International Airport (MDW) 5 times a day.
- Website
- southwest.com
Flights from Sangster International Airport to Chicago Midway International Airport
- Ave. Duration
- 4h 10m
- When
- Saturday
- Estimated price
- $250–1,200
Flights from Sangster International Airport to Chicago Midway International Airport via Orlando
- Ave. Duration
- 7h 27m
- When
- Every day
- Estimated price
- $250–1,200
- Website
- delta.com
Flights from Sangster International Airport to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 8h 26m
- When
- Every day
- Estimated price
- $250–1,200
Flights from Sangster International Airport to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 6h 31m
- When
- Every day
- Estimated price
- $170–800
Flights from Sangster International Airport to South Bend via Atlanta
- Ave. Duration
- 6h 28m
- When
- Every day
- Estimated price
- $220–1,000
Flights from Sangster International Airport to South Bend via Detroit
- Ave. Duration
- 6h 45m
- When
- Friday
- Estimated price
- $240–1,100
- Website
- flyfrontier.com
Flights from Sangster International Airport to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 8h 24m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $440–1,100
Flights from Sangster International Airport to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 8h 50m
- When
- Thursday
- Estimated price
- $310–800
- Website
- aa.com
Flights from Sangster International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 56m
- When
- Every day
- Estimated price
- $170–800
Flights from Sangster International Airport to South Bend via Charlotte
- Ave. Duration
- 8h 48m
- When
- Every day
- Estimated price
- $220–1,000
- Website
- united.com
Flights from Sangster International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 26m
- When
- Every day
- Estimated price
- $170–800
Flights from Sangster International Airport to South Bend via Chicago O'Hare International Airport
- Ave. Duration
- 6h 55m
- When
- Every day
- Estimated price
- $230–1,100
- Website
- jetblue.com
Flights from Sangster International Airport to Chicago O'Hare International Airport via Fort Lauderdale
- Ave. Duration
- 8h 34m
- When
- Every day
- Estimated price
- $170–800
- Website
- flybreeze.com
Flights from Sangster International Airport to South Bend via Orlando
- Ave. Duration
- 5h 56m
- When
- Thursday and Sunday
- Estimated price
- $330–1,600
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Hourly
- Estimated price
- $14–17
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $14–17
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Every 4 hours
- Estimated price
- $4–16
- Schedules at
- Northern Indiana Commuter Transportation District
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