Are there nonstop flights from New Haven (HVN) to Chicago (MDW)?

No. The fastest connection is via Cleveland, about 2h 28m of total flying time.

What is the fastest connection from New Haven (HVN) to Chicago (MDW)?

via Cleveland ≈ 2h 28m, via Detroit ≈ 2h 28m, via Baltimore ≈ 2h 37m (estimated flying time, excluding layovers).

Tweed New Haven Airport (HVN) to Chicago Midway International Airport (MDW)・1,237 km

No nonstop flights. The fastest connection is via Cleveland (CLE), about 2h 28m of flying time (layover not included).

None.

14 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.