Naples to Chicago (APF–MDW) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
APF–MDW had nonstop service, last on the schedule in July 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 1,132 miles in 2h 22m.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| SGX SGX | 0 | – | – | – | – | – |
On-Time Performance
Other ways to reach Chicago from Naples
| Metric | APF→MDW | RSW→MDW | PGD→MDW |
|---|---|---|---|
| Distance from APF | – | 26 mi | 55 mi |
| Nonstop airlines | – | 3 | 1 |
| Weekly flights | – | 34 | 3 |
| Flight time | 2h 22m | 2h 40m | 2h 48m |
Travel Essentials
APF: EDT · MDW: CDT
When it's 6:00 PM in Naples, it's 5:00 PM in Chicago.
APF–MDW Quick Facts
Frequently Asked Questions
Flights from APF to MDW
Naples Municipal Airport (APF) and Chicago Midway International Airport (MDW) had nonstop service, last on the schedule in July 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.
APF to MDW Flight Duration and Schedule
Nonstop flight time from APF to MDW is about 2 hours 22 minutes gate to gate. The route covers a distance of 1,132 miles (1,822 km).
Connecting Options and Alternatives
Nearby alternative airports include Fort Myers (RSW), Punta Gorda (PGD) and Miami (OPF).