Southwest AirlinesWN58% on time
Flights WN2717 06:50 Mo Th Fr · WN4418 07:10 Tu We Sa Su · WN3390 11:55 Mo Th Fr · WN3394 17:25 Mo Th Fr
live
Direct flights from Fort Myers (RSW) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 58% of the last 12 operated flights arrived within 15 minutes of schedule. The median arrival is 14 minutes late. No cancellations were recorded across the 12 tracked flights. The nonstop covers 1,782 km, an estimated 2 hours 47 minutes in the air. Measured by Pro Flight Search from live flight boards at Fort Myers and Chicago. Updated 9 September 2026 at 14:39 UTC.
RSW
Fort Myers
smooth · +10
MDW
Chicago
smooth · +3
1,782 km · ~2h 47m est.
Runs rough · 1 airline · 7x weekly · nonstop
58% on time
of the last 12 operated RSW → MDW flights arrived within 15 minutes
Median arrival delay is +14 min. 0 of 12 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Median arrival+14 minacross the last 12 operated legs
Flight time~2h 47mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 12
The week
scheduled departures · origin local time06121824
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Southwest Airlines
Each mark is a scheduled departure at its origin-local time, observed operating in the last 7 days. Today is highlighted.
Who flies it
observed on the boards · 7 daysHistory
operated legs · board outcomesActual board outcomes rather than schedules, paired departure and arrival per flight and day.
Full board history, day by day →
Airports right now
live boardsWeather lens
Current conditions put the pressure at RSW and MDW: 42% odds of a 15+ minute delay and around +11 min expected when it bites, measured from this route's own weather-matched delay history. See live delays → · Weather risk by airport →
next sweep in 120s
How the Fort Myers to Chicago route actually runs
Pro Flight Search records official board updates for nonstop RSW to MDW flights through the day: schedules, estimates, gate pushes and actual departures. The verdict above comes from operated flights, so it reflects what this route does rather than what the timetable promises.
Planning around a delay? Live airport delays · Weather delay risk map · Will a delayed flight be cancelled? · Do planes make up time in the air? · How we measure
Cite this data
Journalists, bloggers, and researchers may cite this page with attribution and a link to Pro Flight Search.
Suggested citation
Pro Flight Search — Fort Myers (RSW) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/RSW-MDW
RSW to MDW questions
Is RSW–MDW running on time right now?
Smooth skies ahead. The departure side at RSW is the weaker end, route health score 89/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on RSW–MDW?
Operators schedule morning departures around 06:50 and evening departures around 17:25 from RSW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the MDW delay card to confirm conditions when you'd arrive.
How long is the flight from RSW to MDW?
Great-circle distance is 1,782 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 156–183 min gate-to-gate on this route.
How often does RSW–MDW fly?
Southwest Airlines runs the route with about 17 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.
.