Direct (non-stop) flights from Chicago to Montego Bay

All flight schedules from Chicago Midway International , Illinois , USA to Sangster International, Jamaica. This route is operated by Southwest Airlines and the flight time is 4 hours and 00 minutes. The distance is 1719 miles.

Monthly schedule
Week schedules
Airlines
Aircrafts
Price search
MDW Chicago Midway International
USA
Chicago , IL , USA
MBJ Sangster International
Jamaica
Montego Bay, Jamaica
CHANGE DIRECTION
Flight time
4h 00m
Flight distance
1719mi, 2766km
Flights from Chicago to Montego Bay route map
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USA
USA
MDW
Chicago , IL
aircraft image
Jamaica
Jamaica
MBJ
Montego Bay
Distance
1719 miles · (2766 km)
CHANGE DIRECTION
Flight time
4 hours and 00 minutes

Airlines with direct flights from Chicago (MDW) to Montego Bay (MBJ)

  • Southwest Airlines
    S
    M
    T
    W
    T
    F
    S
    Begins in 2026-11-21
    Low-cost airline
    2 weekly flights
FLIGHTS WITH STOPS
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MDW MBJ
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MONTHLY
WN
WEEKLY

Chicago (MDW) to Montego Bay (MBJ) flight schedule

The monthly calendar shows every direct flight departure from Chicago Midway International (MDW) with all airlines. Click on a date to see a list of flights or search for the best prices.

Southwest

View return flights from MBJ to MDW

Southwest Airlines flight schedule from Chicago to Montego Bay

All weekly departures with Southwest Airlines. The week calendar shows every flight departure from Chicago (MDW) to Montego Bay (MBJ). Click on a blue date to see a list of flights.

Week 47 (Nov 16 - Nov 22)
  • Week 47 (Nov 16 - Nov 22)
  • Week 48 (Nov 23 - Nov 29)
  • Week 49 (Nov 30 - Dec 6)
  • Week 50 (Dec 7 - Dec 13)
  • Week 51 (Dec 14 - Dec 20)
  • Week 52 (Dec 21 - Dec 27)
  • Week 53 (Dec 28 - Jan 3)
  • Week 1 (Jan 4 - Jan 10)
  • Week 2 (Jan 11 - Jan 17)
  • Week 3 (Jan 18 - Jan 24)
  • Week 4 (Jan 25 - Jan 31)
  • Week 5 (Feb 1 - Feb 7)
  • Week 6 (Feb 8 - Feb 14)
  • Week 7 (Feb 15 - Feb 21)
  • Week 8 (Feb 22 - Feb 28)
  • Week 9 (Mar 1 - Mar 7)
  • Week 10 (Mar 8 - Mar 14)
  • Week 11 (Mar 15 - Mar 21)
  • Week 12 (Mar 22 - Mar 28)
  • Week 13 (Mar 29 - Apr 4)
  • Week 14 (Apr 5 - Apr 11)
  • Week 15 (Apr 12 - Apr 18)
  • Week 16 (Apr 19 - Apr 25)
  • Week 17 (Apr 26 - May 2)
  • Week 18 (May 3 - May 9)
  • Week 19 (May 10 - May 16)
  • Week 20 (May 17 - May 23)
  • Week 21 (May 24 - May 30)
Flight
Mon
Nov 16
Tue
Nov 17
Wed
Nov 18
Thu
Nov 19
Fri
Nov 20
Sat
Nov 21
Sun
Nov 22
WN1042
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08:05
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Flight time
3h 55m - 4h 00m

JM
Arriving at Sangster (MBJ)

Sangster International (MBJ) is the largest airport in Jamaica and is based in Montego Bay. You can fly to 45 destinations with 23 airlines in scheduled passenger traffic.

Show all flights from MBJ

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US
Departing from Chicago Midway (MDW) , Illinois

Chicago Midway International (MDW) is a large airport in USA. You can fly to 95 destinations with 6 airlines in scheduled passenger traffic.

Show all flights from MDW

Airlines with alternative airports from Chicago to Montego Bay

The airlines below are departing from or arriving to other airports in the same city or very close.

American Airlines
Oneworld
Chicago O Hare International Sangster International
Duration
4 hours and 16 minutes
United
Star Alliance
Chicago O Hare International Sangster International
Duration
4 hours and 10 minutes
Show detailed flight schedule from ORD to MBJ

Airlines with direct flights from Chicago to Montego Bay in the past

  • Frontier Airlines
    Last flight was scheduled 2023-07-01

Chicago - Montego Bay flight price statistics

$660
Approximate

The numbers are avarage prices found based on user searches for direct flights between Chicago Midway International and Sangster International. Its calculated from the cheapest prices found per month for a round-trip with 1 adult and can vary depending on the amount of data we have for this particular route.

N/A
Jan
$593
Feb
$313
Mar
$202
Apr
$202
May
$485
Jun
$490
Jul
$427
Aug
N/A
Sep
N/A
Oct
$1954
Nov
$1869
Dec

Approximate prices for one round-trip flight from Chicago (MDW) to Montego Bay (MBJ). Graph is not to scale.

CLICK HERE FOR EXACT PRICES

Type of aircraft(s) on this route

Below is a list of aircraft types we have within our database with flights on this route. You can also see the aircrafts seat capacity together with classes.

Boeing 737MAX 8 Passenger
Southwest Airlines
Boeing 737MAX 8 Passenger illustration
Boeing 737MAX 8 Passenger illustration
175 seats
 (All economy)
ROUTE EXPLORING

Chicago Midway International - all destinations

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Chicago flight map

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Round trip
1 adult
Economy

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Frequently asked questions FAQ

  • The flight between Chicago (MDW) and Montego Bay (MBJ) typically takes about 3 hour and 55 minute.
  • The flight number is WN1042 and it's operated by Southwest Airlines.
  • From Chicago you will fly out from Chicago Midway International (MDW) and you will be landing at Sangster International (MBJ).
  • Boeing 737 flies this route operated by Southwest.
  • Southwest have non-stop flights to Montego Bay.
VIEW IN
MAP EXPLORER Flights from Chicago to Montego Bay route map
Non-stop flights from MDW to MBJ
1719 miles (2766 km) · 4 hours and 00 minutes
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Popular routes from Chicago

Southwest Airlines Southwest Airlines routes

Chicago (MDW) - Phoenix (PHX)

US

Chicago (MDW) - Orlando (MCO)

US

Chicago (MDW) - New York (LGA)

US

Chicago (MDW) - Las Vegas (LAS)

US

Chicago (MDW) - Washington (DCA)

US

For more destinations from Chicago with Southwest Airlines (WN), check out the Southwest Airlines route map .

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