Are there nonstop flights from Chicago (MDW) to Key West (EYW)?

No. The fastest connection is via Tampa, about 3h 20m of total flying time.

What is the fastest connection from Chicago (MDW) to Key West (EYW)?

via Tampa ≈ 3h 20m, via Atlanta ≈ 3h 21m, via Indianapolis ≈ 3h 21m (estimated flying time, excluding layovers).

Chicago Midway International Airport (MDW) to Key West International Airport (EYW)・1,994 km

No nonstop flights. The fastest connection is via Tampa (TPA), about 3h 20m of flying time (layover not included).

None.

18 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.