Are there nonstop flights from New York (LGA) to Chicago (MDW)?

Yes. Southwest Airlines fly this route. Flight time is about 1h 52m.

What is the fastest connection from New York (LGA) to Chicago (MDW)?

via Cleveland ≈ 2h 22m, via Detroit ≈ 2h 23m, via Pittsburgh ≈ 2h 24m (estimated flying time, excluding layovers).

LaGuardia Airport (LGA) to Chicago Midway International Airport (MDW)・1,164 km

Nonstop flights available (1 airline). Flight time about 1h 52m. Nonstop return flights also operate.

34 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.