Southwest AirlinesWN89% on time
Flights WN359 varies Mo Tu We Th Fr Su · WN4895 08:55 Sa · WN806 10:00 Mo Th Fr · WN2610 11:45 Mo Th Fr Su
live
Direct flights from Orlando (MCO) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 89% of the last 9 operated flights arrived within 15 minutes of schedule. The median arrival is 5 minutes early. No cancellations were recorded across the 9 tracked flights. The nonstop covers 1,595 km, an estimated 2 hours 33 minutes in the air. Measured by Pro Flight Search from live flight boards at Orlando and Chicago. Updated 11 September 2026 at 13:38 UTC.
MCO
Orlando
smooth · +0
MDW
Chicago
smooth · +0
1,595 km · ~2h 33m est.
Runs reliable · 1 airline · 7x weekly · nonstop
89% on time
of the last 9 operated MCO → MDW flights arrived within 15 minutes
Median arrival delay is −5 min. 0 of 9 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Median arrival−5 minacross the last 9 operated legs
Flight time~2h 33mestimated from route distance
Weekly departures7x1 direct airline on the leg
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 MCO 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 Orlando to Chicago route actually runs
Pro Flight Search records official board updates for nonstop MCO 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 — Orlando (MCO) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/MCO-MDW
MCO to MDW questions
Is MCO–MDW running on time right now?
Smooth skies ahead. Both endpoints currently score the same, route health score 100/100. The airports section above carries the live status and delay window at both ends.
How long is the flight from MCO to MDW?
Great-circle distance is 1,595 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 143–167 min gate-to-gate on this route.
How often does MCO–MDW fly?
Southwest Airlines runs the route with about 42 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.
What does the route health score measure?
A blend of departure-side delay at MCO and arrival-side delay at MDW, computed from rolling delay windows (refreshed every 40 minutes) with a daily-rollup fallback. Current MVFR, IFR, or LIFR endpoint weather caps the score when flight rules can limit throughput. Higher is healthier: 100 means operations are clean at both ends.
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