Are there nonstop flights from Montego Bay (MBJ) to Chicago (MDW)?

Yes. Southwest Airlines fly this route. Flight time is about 3h 44m.

What is the fastest connection from Montego Bay (MBJ) to Chicago (MDW)?

via Miami ≈ 4h 14m, via Atlanta ≈ 4h 14m, via Orlando ≈ 4h 15m (estimated flying time, excluding layovers).

Sangster International Airport (MBJ) to Chicago Midway International Airport (MDW)・2,752 km

Nonstop flights available (1 airline). Flight time about 3h 44m. Nonstop return flights also operate.

19 one-stop options, sorted by estimated flying time. Tap one to see the airlines on each leg and booking links.

Times are estimated from distance. Check schedules, frequency and availability with the airline or a booking site.