Are there nonstop flights from Chicago (MDW) to San José del Cabo (SJD)?

Yes. Southwest Airlines fly this route. Flight time is about 3h 55m.

What is the fastest connection from Chicago (MDW) to San José del Cabo (SJD)?

via St Louis ≈ 4h 27m, via Dallas-Fort Worth ≈ 4h 27m, via Kansas City ≈ 4h 27m (estimated flying time, excluding layovers).

Chicago Midway International Airport (MDW) to Los Cabos International Airport (SJD)・2,906 km

Nonstop flights available (1 airline). Flight time about 3h 55m. Nonstop return flights also operate.

29 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.