Southwest AirlinesWN
Flights WN8505 10:00 Mo
live
Direct flights from Chicago (ORD) to Chicago (MDW): 2 nonstop departures observed each week across 2 airlines. 14% of the last 7 operated flights arrived within 15 minutes of schedule. The median arrival is 62 minutes late. No cancellations were recorded across the 7 tracked flights. The nonstop covers 25 km, an estimated 32 minutes in the air. Measured by Pro Flight Search from live flight boards at Chicago and Chicago. Updated 20 August 2026 at 16:08 UTC.
ORD
Chicago
smooth · +0
MDW
Chicago
smooth · +0
25 km · ~0h 32m est.
Runs rough · 2 airlines · 2x weekly · nonstop
14% on time
of the last 7 operated ORD → MDW flights arrived within 15 minutes
Median arrival delay is +62 min. 0 of 7 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
Search live fares for this route →Median arrival+62 minacross the last 7 operated legs
Flight time~0h 32mestimated from route distance
Weekly departures2x2 direct airlines on the leg
Current nonstop fares
ORD → MDW · one way · economy · 1 adult
TodayChecking…Direct airline fares
TomorrowChecking…Direct airline fares
In one weekChecking…Direct airline fares
The week
scheduled departures · origin local time06121824
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Southwest AirlinesUnited 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 daysUnited AirlinesUA
Flights UA3752 15:00 Th
History
operated legs · board outcomes08-191I290dep +66 → arr+67
08-171I438dep +20 → arr+0
08-161I586dep +41 → arr+412
08-161I965dep +49 → arr+57
08-13LXJ422dep +54 → arr+62
Actual 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 ORD and MDW: 49% odds of a 15+ minute delay and around +16 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 Chicago to Chicago route actually runs
Pro Flight Search tracks every published board update for nonstop ORD to MDW flights: 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. Fares link straight to the operating airline with no markups.
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 — Chicago (ORD) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.
Canonical URL
How we measure this →
https://proflightsearch.com/search-flights/ORD-MDW
ORD to MDW questions
Is ORD–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.
Morning or evening flight on ORD–MDW?
Operators schedule morning departures around 10:00 from ORD. 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 ORD to MDW?
Great-circle distance is 25 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 32–32 min gate-to-gate on this route.
How often does ORD–MDW fly?
2 carriers operate this route, around 2 flights a week between them. Compare carrier days and times in the airline list above.
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