Chicago (MDW) to Montego Bay (MBJ) flights
One airline flies nonstop from Chicago (MDW) to Montego Bay (MBJ): Southwest Airlines. The two airports are 1,710 miles (2,752 km) apart. There are also 19 ways to fly it with one stop, through Miami, Orlando and Fort Lauderdale and more.
Airlines flying nonstop from MDW to MBJ
- Southwest AirlinesNot in an allianceWho books it
MDW to MBJ with one stop
19 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Miami (MIA)Southwest Airlines, then American Airlines
- Via Orlando (MCO)Southwest Airlines the whole way
- Via Fort Lauderdale (FLL)Southwest Airlines, then JetBlue Airways
- Via Atlanta (ATL)Delta Air Lines and Frontier Airlines the whole way
- Via Tampa (TPA)Southwest Airlines, then Breeze Airways
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Charlotte (CLT)Southwest Airlines, then American 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)Southwest Airlines, then NeosNO
- Via Philadelphia (PHL)Southwest Airlines, then American Airlines and Frontier Airlines
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Houston (HOU)Southwest Airlines the whole way
- Via Dallas (DFW)Frontier Airlines, then American Airlines
MDW to MBJ: common questions
Which airlines fly nonstop from MDW to MBJ?
Southwest Airlines flies nonstop from Chicago (MDW) to Montego Bay (MBJ).
How far is Chicago from Montego Bay by plane?
Chicago (MDW) and Montego Bay (MBJ) 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 MDW to MBJ cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to MBJ with taxes and fees.
Where can I connect between Chicago and Montego Bay?
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.