Flight Schedules
Last Updated: Thu, 2 May, 2024
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13:00 - 17:10MBJ - MDW
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13:00 (MBJ)Montego Bay Airport
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17:10 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1043)Boeing 737 800 - 4h 10m
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- Boeing 737 800
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13:35 - 17:40MBJ - MDW
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13:35 (MBJ)Montego Bay Airport
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17:40 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1043)Boeing 737 Max 8 Passenger - 4h 05m
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- Boeing 737 Max 8 Passenger
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13:50 - 18:10MBJ - ORD
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13:50 (MBJ)Montego Bay Airport
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18:10 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1160)Boeing 737 800 - 4h 20m
- Direct
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- S
- Boeing 737 800
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14:27 - 18:55MBJ - ORD
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14:27 (MBJ)Montego Bay Airport
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18:55 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 975)Boeing 737 800 - 4h 28m
- Direct
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- S
- Boeing 737 800
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15:20 - 19:25MBJ - MDW
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15:20 (MBJ)Montego Bay Airport
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19:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1043)Boeing 737 Max 8 Passenger - 4h 05m
- Direct
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- T
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- Boeing 737 Max 8 Passenger
Connecting Flights
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12:00 - 16:25MBJ - BWI18:15 - 19:15BWI - MDW
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12:00 (MBJ)Montego Bay Airport18:15 (BWI)Baltimore Washington International Airport
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16:25 (BWI)Baltimore Washington International Airport19:15 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 929)Boeing 737 800 Southwest Airlines (WN 1789)Boeing 737 Max 8 Passenger - 7h 15m (1h 50m)
- BWI Baltimore 1h 50m
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12:00 - 16:25MBJ - BWI18:55 - 20:00BWI - MDW
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12:00 (MBJ)Montego Bay Airport18:55 (BWI)Baltimore Washington International Airport
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16:25 (BWI)Baltimore Washington International Airport20:00 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 929)Boeing 737 800 Southwest Airlines (WN 1789)Boeing 737 800 - 8h (2h 30m)
- BWI Baltimore 2h 30m
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12:00 - 16:25MBJ - BWI18:00 - 20:30BWI - MDW
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12:00 (MBJ)Montego Bay Airport18:00 (BWI)Baltimore Washington International Airport
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16:25 (BWI)Baltimore Washington International Airport20:30 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 929)Boeing 737 800 Southwest Airlines (WN 523)Boeing 737 800 - 8h 30m (1h 35m)
- BWI Baltimore 1h 35m
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12:00 - 16:25MBJ - BWI20:20 - 21:25BWI - MDW
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12:00 (MBJ)Montego Bay Airport20:20 (BWI)Baltimore Washington International Airport
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16:25 (BWI)Baltimore Washington International Airport21:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 929)Boeing 737 800 Southwest Airlines (WN 3059)Boeing 737 700 - 9h 25m (3h 55m)
- BWI Baltimore 3h 55m
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12:00 - 16:25MBJ - BWI21:00 - 22:00BWI - MDW
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12:00 (MBJ)Montego Bay Airport21:00 (BWI)Baltimore Washington International Airport
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16:25 (BWI)Baltimore Washington International Airport22:00 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 929)Boeing 737 800 Southwest Airlines (WN 3059)Boeing 737 Max 8 Passenger - 10h (4h 35m)
- BWI Baltimore 4h 35m
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12:30 - 15:35MBJ - MCO20:40 - 22:25MCO - MDW
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12:30 (MBJ)Montego Bay Airport20:40 (MCO)Orlando International Airport
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15:35 (MCO)Orlando International Airport22:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 273)Boeing 737 800 Southwest Airlines (WN 1328)Boeing 737 700 - 9h 55m (5h 05m)
- MCO Orlando 5h 05m
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13:00 - 15:50MBJ - FLL19:10 - 21:20FLL - MDW
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13:00 (MBJ)Montego Bay Airport19:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
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15:50 (FLL)Fort Lauderdale/Hollywood Intl Airport21:20 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1025)Boeing 737 800 Southwest Airlines (WN 3107)Boeing 737 Max 8 Passenger - 8h 20m (3h 20m)
- FLL Miami 3h 20m
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13:00 - 15:50MBJ - FLL19:10 - 21:25FLL - MDW
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13:00 (MBJ)Montego Bay Airport19:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
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15:50 (FLL)Fort Lauderdale/Hollywood Intl Airport21:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1025)Boeing 737 800 Southwest Airlines (WN 3107)Boeing 737 800 - 8h 25m (3h 20m)
- FLL Miami 3h 20m
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14:00 - 16:45MBJ - FLL19:05 - 21:15FLL - MDW
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14:00 (MBJ)Montego Bay Airport19:05 (FLL)Fort Lauderdale/Hollywood Intl Airport
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16:45 (FLL)Fort Lauderdale/Hollywood Intl Airport21:15 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1025)Boeing 737 800 Southwest Airlines (WN 3107)Boeing 737 Max 8 Passenger - 7h 15m (2h 20m)
- FLL Miami 2h 20m
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14:10 - 16:55MBJ - FLL19:00 - 21:15FLL - MDW
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14:10 (MBJ)Montego Bay Airport19:00 (FLL)Fort Lauderdale/Hollywood Intl Airport
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16:55 (FLL)Fort Lauderdale/Hollywood Intl Airport21:15 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1025)Boeing 737 800 Southwest Airlines (WN 3107)Boeing 737 Max 8 Passenger - 7h 05m (2h 05m)
- FLL Miami 2h 05m
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14:40 - 17:50MBJ - MCO20:40 - 22:25MCO - MDW
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14:40 (MBJ)Montego Bay Airport20:40 (MCO)Orlando International Airport
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17:50 (MCO)Orlando International Airport22:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 293)Boeing 737 800 Southwest Airlines (WN 1328)Boeing 737 700 - 7h 45m (2h 50m)
- MCO Orlando 2h 50m
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15:05 - 18:10MBJ - MCO21:20 - 23:10MCO - MDW
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15:05 (MBJ)Montego Bay Airport21:20 (MCO)Orlando International Airport
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18:10 (MCO)Orlando International Airport23:10 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 273)Boeing 737 800 Southwest Airlines (WN 1328)Boeing 737 800 - 8h 05m (3h 10m)
- MCO Orlando 3h 10m
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15:05 - 18:10MBJ - MCO21:30 - 23:20MCO - MDW
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15:05 (MBJ)Montego Bay Airport21:30 (MCO)Orlando International Airport
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18:10 (MCO)Orlando International Airport23:20 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 273)Boeing 737 800 Southwest Airlines (WN 1328)Boeing 737 Max 8 Passenger - 8h 15m (3h 20m)
- MCO Orlando 3h 20m
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15:05 - 18:10MBJ - MCO21:45 - 23:30MCO - MDW
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15:05 (MBJ)Montego Bay Airport21:45 (MCO)Orlando International Airport
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18:10 (MCO)Orlando International Airport23:30 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 273)Boeing 737 800 Southwest Airlines (WN 1328)Boeing 737 Max 8 Passenger - 8h 25m (3h 35m)
- MCO Orlando 3h 35m
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15:35 - 19:55MBJ - BWI21:55 - 22:55BWI - MDW
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15:35 (MBJ)Montego Bay Airport21:55 (BWI)Baltimore Washington International Airport
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19:55 (BWI)Baltimore Washington International Airport22:55 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 905)Boeing 737 800 Southwest Airlines (WN 2775)Boeing 737 700 - 7h 20m (2h)
- BWI Baltimore 2h
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15:40 - 19:15MBJ - HOU20:50 - 23:25HOU - MDW
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15:40 (MBJ)Montego Bay Airport20:50 (HOU)Houston Hobby Airport
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19:15 (HOU)Houston Hobby Airport23:25 (MDW)Chicago Midway Airport
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Southwest Airlines (WN 1116)Boeing 737 Max 8 Passenger Southwest Airlines (WN 3115)Boeing 737 Max 8 Passenger - 7h 45m (1h 35m)
- HOU Houston 1h 35m
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What’s the fastest flight time from Montego Bay to Chicago?
The fastest flight time for direct flights from Montego Bay to Chicago is 4 hours 5 minutes. Check latest flight schedules & prices on Wego.
How far is Chicago from Montego Bay?
The flight distance between Montego Bay and Chicago is 2761km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 12:00. The last flight of the day departs at 12:00. See the full list of flight times on Wego.
How many airlines offer direct flights from Montego Bay to Chicago?
There are 3 airlines that offer direct flights from Montego Bay to Chicago. Find out the list of airlines on Wego.
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