Are there nonstop flights from Cape Town (CPT) to Chicago (MDW)?

No. The fastest connection is via Newark, about 17h 10m of total flying time.

What is the fastest connection from Cape Town (CPT) to Chicago (MDW)?

via Newark ≈ 17h 10m, via Atlanta ≈ 17h 31m (estimated flying time, excluding layovers).

Cape Town International Airport (CPT) to Chicago Midway International Airport (MDW)・13,691 km

No nonstop flights. The fastest connection is via Newark (EWR), about 17h 10m of flying time (layover not included).

None.

2 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.