Are there nonstop flights from San José (SJO) to Chicago (MDW)?

No. The fastest connection is via Nashville, about 5h 11m of total flying time.

What is the fastest connection from San José (SJO) to Chicago (MDW)?

via Nashville ≈ 5h 11m, via Cancún ≈ 5h 12m, via Atlanta ≈ 5h 13m (estimated flying time, excluding layovers).

Juan Santamaría International Airport (SJO) to Chicago Midway International Airport (MDW)・3,552 km

No nonstop flights. The fastest connection is via Nashville (BNA), about 5h 11m of flying time (layover not included).

None.

16 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.