Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline American Airlines

The cheapest airline(s) flying from Chicago to Montego Bay is American Airlines.

  • American Airlines American Airlines
  • Delta Air Lines Delta Air Lines
  • United Airlines United Airlines
  • Copa Airlines Copa Airlines
  • Frontier Airlines Frontier Airlines
  • JetBlue Airways JetBlue Airways
  • Air Canada Air Canada
  • WestJet WestJet
Cheapest Month March

Travel Period: June 2024 - May 2025

The cheapest month(s) to fly from Chicago to Montego Bay is March.

  • Jun 2024
  • Jul 2024
  • Aug 2024
  • Sep 2024
  • Oct 2024
  • Nov 2024
  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
Cheapest Day of the Week Wednesday

The cheapest day(s) of the week to fly from Chicago to Montego Bay is Wednesday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday
Cheapest Time 7am

The cheapest time of the day to fly from Chicago to Montego Bay is in the morning.

Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm

Flight Schedules

Last Updated: Thu, 2 May, 2024

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  • Airline Filter by Airline
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  • Total Duration
    • Shortest
    • Longest
  • Stopover
    All
  • Availability
    • M
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    • S
  • 08:20 - 12:16
    ORD - MBJ
  • 08:20 (ORD)Chicago O'Hare International Airport
  • 12:16 (MBJ)Montego Bay Airport
  • American Airlines (AA 975)Boeing 737 800
  • 3h 56m
  • Direct
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Boeing 737 800
  • 08:45 - 12:45
    ORD - MBJ
  • 08:45 (ORD)Chicago O'Hare International Airport
  • 12:45 (MBJ)Montego Bay Airport
  • United Airlines (UA 1146)Boeing 737 800
  • 4h
  • Direct
    • M
    • T
    • W
    • T
    • -
    • S
    • S
  • Boeing 737 800
  • 09:05 - 13:00
    MDW - MBJ
  • 09:05 (MDW)Chicago Midway Airport
  • 13:00 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 1042)Boeing 737 800
  • 3h 55m
  • Direct
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 800
  • 10:05 - 14:00
    MDW - MBJ
  • 10:05 (MDW)Chicago Midway Airport
  • 14:00 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 1042)Boeing 737 800
  • 3h 55m
  • Direct
    • -
    • -
    • -
    • -
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    • S
    • -
  • Boeing 737 800
  • 10:25 - 14:20
    MDW - MBJ
  • 10:25 (MDW)Chicago Midway Airport
  • 14:20 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 1042)Boeing 737 Max 8 Passenger
  • 3h 55m
  • Direct
    • -
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  • Boeing 737 Max 8 Passenger

Connecting Flights

  • 05:40 - 09:10
    MDW - MCO
    13:00 - 14:05
    MCO - MBJ
  • 05:40 (MDW)Chicago Midway Airport
    13:00 (MCO)Orlando International Airport
  • 09:10 (MCO)Orlando International Airport
    14:05 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 332)Boeing 737 800
    Southwest Airlines (WN 272)Boeing 737 800
  • 8h 25m (3h 50m)
  • MCO Orlando 3h 50m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 12:00 - 13:10
    MCO - MBJ
    05:45 - 07:10
    MDW - BNA
  • 12:00 (MCO)Orlando International Airport
    05:45 (MDW)Chicago Midway Airport
  • 13:10 (MBJ)Montego Bay Airport
    07:10 (BNA)Nashville Airport
  • Southwest Airlines (WN 292)Boeing 737 800
    Southwest Airlines (WN 270)Boeing 737 700
  • 7h 25m (1h 55m)
  • MBJ 1h 55m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:00 - 08:55
    MDW - BWI
    12:05 - 14:35
    BWI - MBJ
  • 06:00 (MDW)Chicago Midway Airport
    12:05 (BWI)Baltimore Washington International Airport
  • 08:55 (BWI)Baltimore Washington International Airport
    14:35 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 1823)Boeing 737 800
    Southwest Airlines (WN 906)Boeing 737 800
  • 8h 35m (3h 10m)
  • BWI Baltimore 3h 10m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 06:00 - 09:55
    MDW - FLL
    11:10 - 12:00
    FLL - MBJ
  • 06:00 (MDW)Chicago Midway Airport
    11:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
  • 09:55 (FLL)Fort Lauderdale/Hollywood Intl Airport
    12:00 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 2331)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 583)Boeing 737 800
  • 6h (1h 15m)
  • FLL Miami 1h 15m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 06:00 - 09:30
    MDW - MCO
    13:00 - 14:05
    MCO - MBJ
  • 06:00 (MDW)Chicago Midway Airport
    13:00 (MCO)Orlando International Airport
  • 09:30 (MCO)Orlando International Airport
    14:05 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 332)Boeing 737 700
    Southwest Airlines (WN 272)Boeing 737 800
  • 8h 05m (3h 30m)
  • MCO Orlando 3h 30m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 06:05 - 10:05
    MDW - FLL
    12:50 - 13:40
    FLL - MBJ
  • 06:05 (MDW)Chicago Midway Airport
    12:50 (FLL)Fort Lauderdale/Hollywood Intl Airport
  • 10:05 (FLL)Fort Lauderdale/Hollywood Intl Airport
    13:40 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 2331)Boeing 737 700
    Southwest Airlines (WN 583)Boeing 737 800
  • 7h 35m (2h 45m)
  • FLL Miami 2h 45m
    • -
    • -
    • -
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    • -
    • S
    • -
  • 06:10 - 10:05
    MDW - FLL
    11:10 - 12:00
    FLL - MBJ
  • 06:10 (MDW)Chicago Midway Airport
    11:10 (FLL)Fort Lauderdale/Hollywood Intl Airport
  • 10:05 (FLL)Fort Lauderdale/Hollywood Intl Airport
    12:00 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 2331)Boeing 737 700
    Southwest Airlines (WN 583)Boeing 737 800
  • 5h 50m (1h 05m)
  • FLL Miami 1h 05m
    • -
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    • W
    • -
    • -
    • -
    • -
  • 06:15 - 09:45
    MDW - MCO
    12:00 - 13:10
    MCO - MBJ
  • 06:15 (MDW)Chicago Midway Airport
    12:00 (MCO)Orlando International Airport
  • 09:45 (MCO)Orlando International Airport
    13:10 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 332)Boeing 737 700
    Southwest Airlines (WN 292)Boeing 737 800
  • 6h 55m (2h 15m)
  • MCO Orlando 2h 15m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 13:00 - 14:05
    MCO - MBJ
    06:20 - 07:45
    MDW - BNA
  • 13:00 (MCO)Orlando International Airport
    06:20 (MDW)Chicago Midway Airport
  • 14:05 (MBJ)Montego Bay Airport
    07:45 (BNA)Nashville Airport
  • Southwest Airlines (WN 272)Boeing 737 800
    Southwest Airlines (WN 270)Boeing 737 Max 8 Passenger
  • 7h 45m (2h 20m)
  • MBJ 2h 20m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 06:30 - 10:10
    ORD - MCO
    13:00 - 14:05
    MCO - MBJ
  • 06:30 (ORD)Chicago O'Hare International Airport
    13:00 (MCO)Orlando International Airport
  • 10:10 (MCO)Orlando International Airport
    14:05 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 2985)Boeing 737 700
    Southwest Airlines (WN 272)Boeing 737 800
  • 7h 35m (2h 50m)
  • MCO Orlando 2h 50m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 13:00 - 14:05
    MCO - MBJ
    06:30 - 07:45
    MDW - STL
  • 13:00 (MCO)Orlando International Airport
    06:30 (MDW)Chicago Midway Airport
  • 14:05 (MBJ)Montego Bay Airport
    07:45 (STL)St Louis Lambert Intl Airport
  • Southwest Airlines (WN 272)Boeing 737 800
    Southwest Airlines (WN 5846)Boeing 737 800
  • 7h 35m (1h 55m)
  • MBJ 1h 55m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 06:35 - 10:05
    MDW - MCO
    13:00 - 14:05
    MCO - MBJ
  • 06:35 (MDW)Chicago Midway Airport
    13:00 (MCO)Orlando International Airport
  • 10:05 (MCO)Orlando International Airport
    14:05 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 332)Boeing 737 800
    Southwest Airlines (WN 272)Boeing 737 800
  • 7h 30m (2h 55m)
  • MCO Orlando 2h 55m
    • M
    • -
    • -
    • T
    • F
    • -
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  • 13:00 - 14:05
    MCO - MBJ
    07:05 - 09:55
    MDW - ATL
  • 13:00 (MCO)Orlando International Airport
    07:05 (MDW)Chicago Midway Airport
  • 14:05 (MBJ)Montego Bay Airport
    09:55 (ATL)Atlanta Hartsfield-Jackson Intl Airport
  • Southwest Airlines (WN 272)Boeing 737 800
    Southwest Airlines (WN 1572)Boeing 737 800
  • 7h (1h 40m)
  • MBJ 1h 40m
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 07:15 - 10:05
    MDW - BWI
    12:10 - 14:40
    BWI - MBJ
  • 07:15 (MDW)Chicago Midway Airport
    12:10 (BWI)Baltimore Washington International Airport
  • 10:05 (BWI)Baltimore Washington International Airport
    14:40 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 5903)Boeing 737 700
    Southwest Airlines (WN 906)Boeing 737 Max 8 Passenger
  • 7h 25m (2h 05m)
  • BWI Baltimore 2h 05m
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 08:05 - 10:50
    MDW - BWI
    12:05 - 14:35
    BWI - MBJ
  • 08:05 (MDW)Chicago Midway Airport
    12:05 (BWI)Baltimore Washington International Airport
  • 10:50 (BWI)Baltimore Washington International Airport
    14:35 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 5903)Boeing 737 700
    Southwest Airlines (WN 906)Boeing 737 800
  • 6h 30m (1h 15m)
  • BWI Baltimore 1h 15m
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 08:10 - 11:45
    MDW - MCO
    13:00 - 14:05
    MCO - MBJ
  • 08:10 (MDW)Chicago Midway Airport
    13:00 (MCO)Orlando International Airport
  • 11:45 (MCO)Orlando International Airport
    14:05 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 2966)Boeing 737 700
    Southwest Airlines (WN 272)Boeing 737 800
  • 5h 55m (1h 15m)
  • MCO Orlando 1h 15m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 08:15 - 11:10
    MDW - BWI
    12:05 - 14:35
    BWI - MBJ
  • 08:15 (MDW)Chicago Midway Airport
    12:05 (BWI)Baltimore Washington International Airport
  • 11:10 (BWI)Baltimore Washington International Airport
    14:35 (MBJ)Montego Bay Airport
  • Southwest Airlines (WN 5903)Boeing 737 800
    Southwest Airlines (WN 906)Boeing 737 800
  • 6h 20m (55m)
  • BWI Baltimore 55m
    • M
    • -
    • -
    • T
    • F
    • -
    • -
No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
What’s the fastest flight time from Chicago to Montego Bay?

The fastest flight time for direct flights from Chicago to Montego Bay is 3 hours 55 minutes. Check latest flight schedules & prices on Wego.

How far is Montego Bay from Chicago?

The flight distance between Chicago and Montego Bay 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 05:40. The last flight of the day departs at 05:40. See the full list of flight times on Wego.

How many airlines offer direct flights from Chicago to Montego Bay?

There are 3 airlines that offer direct flights from Chicago to Montego Bay. Find out the list of airlines on Wego.