Montego Bay to Chicago (MBJ–MDW) — Airlines, Schedules & Connections

MBJ Airport Page →
1,710 mi airlines charter/private 2/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 14 1-stop flights Verified 4w ago
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-Stop connections via 10 hubs
MCO Orlando 6h 1m B6WN → WN Orlando (MCO) to Chicago flights
ATL Atlanta 6h 2m DLF9VS → AFAMDL Atlanta (ATL) to Chicago flights
BWI Baltimore 6h 28m LXJWN → WN Baltimore (BWI) to Chicago flights
CLT Charlotte 6h 28m AA → EJAWN Charlotte (CLT) to Chicago flights
MIA Miami 6h 28m AAIIQR → LXJWN Miami (MIA) to Chicago flights
FLL Fort Lauderdale 6h 31m B6 → WN Fort Lauderdale (FLL) to Chicago flights
HOU Houston 6h 31m WN → WN Houston (HOU) to Chicago flights
BOS Boston 9h B6 → UAWN Boston (BOS) to Chicago flights
PHL Philadelphia 17h 2m AAF9 → WN Philadelphia (PHL) to Chicago flights
DEN Denver 18h 55m UA → WN Denver (DEN) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Montego Bay to Chicago
Connecting service available through multiple hubs.
1 Airlines 1,710 mi 4h 5m nonstop

MBJ–MDW had nonstop service from Southwest Airlines, last on the schedule in July 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 1,710 miles in 4h 5m.

Also explore MBJ Routes MDW Routes MBJ Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to Montego Bay flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop MBJ–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 2 – – – – –
Alliance coverage
Unaffiliated: WN (2 flights/wk, 100%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for MBJ to MDW.
1-STOP
One-Stop Connections
14
Hubs
~6h
Fastest
~27h
Longest
MCO ~6h 1m ATL ~6h 2m STL ~6h 20m BWI ~6h 28m CLT ~6h 28m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,141
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
MBJ → MDW
64%
Moderate delays possible. Allow buffer time.
Arriving
64%
Return
MDW → MBJ
58%
Frequent delays expected. Consider flexible booking.
Departing
58%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
0h
Chicago is 0 hours the same as Montego Bay.
MBJ: EST · MDW: CDT

When it's 6:00 PM in Montego Bay, it's 6:00 PM in Chicago.
Distance & Flight Time
1,710 mi / 2,752 km
Nonstop flight time is approximately 4h 5m gate to gate.
Facts

MBJ–MDW Quick Facts

Key statistics for the Montego Bay to Chicago route.
Route details
Distance1,710 mi / 2,752 km
Flight time4h 5m
Time difference0 hours
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: MBJ
Full nameSangster International Airport
IATA / ICAOMBJ / MKJS
TimezoneAmerica/Jamaica
Passengers/yr5.3M
Elevation4 ft / 1 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about MBJ to MDW flights.
Nonstop flights from Sangster International Airport to Chicago Midway International Airport take about 4h 5m gate to gate. The route covers 1,710 miles.
1 airline operated the nonstop from MBJ to MDW: Southwest Airlines. The last scheduled nonstop was in July 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in July 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 4h 5m.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Orlando, Hartsfield Jackson Atlanta and Baltimore/Washington International Thurgood Marshall.
Yes, return flights from MDW to MBJ are available. Use the direction toggle at the top to view the return schedule.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from MBJ to MDW

Sangster International Airport (MBJ) and Chicago Midway International Airport (MDW) had nonstop service from Southwest Airlines, last on the schedule in July 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.

MBJ to MDW Flight Duration and Schedule

Nonstop flight time from MBJ to MDW is about 4 hours 5 minutes gate to gate. The route covers a distance of 1,710 miles (2,752 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Orlando, Hartsfield Jackson Atlanta and Baltimore/Washington International Thurgood Marshall. Two-stop connections are also available via intermediate hubs.