Montego Bay (MBJ) to Chicago (MDW) flights
One airline flies nonstop from Montego Bay (MBJ) to Chicago (MDW): Southwest Airlines. The two airports are 1,710 miles (2,752 km) apart. There are also 18 ways to fly it with one stop, through Miami, Orlando and Fort Lauderdale and more.
Airlines flying nonstop from MBJ to MDW
- Southwest AirlinesNot in an allianceWho books it
MBJ to MDW with one stop
18 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Miami (MIA)American Airlines, then Southwest Airlines
- Via Orlando (MCO)Southwest Airlines the whole way
- Via Fort Lauderdale (FLL)JetBlue Airways, then Southwest Airlines
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way
- Via Tampa (TPA)Breeze Airways, then Southwest Airlines
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Cancun (CUN)TUIfly Netherlands, then Southwest AirlinesOR
- Via Philadelphia (PHL)American Airlines and Frontier Airlines, then Southwest Airlines
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Houston (HOU)Southwest Airlines the whole way
- Via Dallas (DFW)American Airlines, then Frontier Airlines
MBJ to MDW: common questions
Which airlines fly nonstop from MBJ to MDW?
Southwest Airlines flies nonstop from Montego Bay (MBJ) to Chicago (MDW).
How far is Montego Bay from Chicago by plane?
Montego Bay (MBJ) and Chicago (MDW) are 1,710 miles (2,752 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does MBJ to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MBJ to MDW with taxes and fees.
Where can I connect between Montego Bay and Chicago?
The most direct connections are through Miami (MIA), Orlando (MCO), Fort Lauderdale (FLL), Atlanta (ATL) and Tampa (TPA). On 9 of them the same airline flies both flights, for example Southwest Airlines through Orlando.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.