Are there nonstop flights from Chicago (MDW) to San Juan (SJU)?

Yes. Southwest Airlines fly this route. Flight time is about 4h 24m.

What is the fastest connection from Chicago (MDW) to San Juan (SJU)?

via Charlotte ≈ 4h 54m, via Indianapolis ≈ 4h 54m, via Raleigh/Durham ≈ 4h 55m (estimated flying time, excluding layovers).

Chicago Midway International Airport (MDW) to Luis Munoz Marin International Airport (SJU)・3,314 km

Nonstop flights available (1 airline). Flight time about 4h 24m. Nonstop return flights also operate.

30 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.