Flights UA3759 18:25 Tu · UA3757 22:55 Mo · UA3753 23:20 Mo · UA3755 23:20 Mo
Direct flights from Chicago (MDW) to Chicago (ORD): 2 nonstop departures observed each week across 1 airline. 63% of the last 8 operated flights arrived within 15 minutes of schedule. The median arrival is 11 minutes late. No cancellations were recorded across the 8 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 9 October 2026 at 14:30 UTC.
of the last 8 operated MDW → ORD flights arrived within 15 minutes
Median arrival delay is +11 min. 0 of 8 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →
The week
scheduled departures · origin local timeEach 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 MDW and ORD: 42% odds of a 15+ minute delay and around +12 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 records official board updates for nonstop MDW to ORD 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
Journalists, bloggers, and researchers may cite this page with attribution and a link to Pro Flight Search.
Pro Flight Search — Chicago (MDW) to Chicago (ORD) route reliability, measured from operated flights on official airport boards.
https://proflightsearch.com/search-flights/MDW-ORD
MDW to ORD questions
Is MDW–ORD running on time right now?
Mostly on schedule. The departure side at MDW is the weaker end, route health score 79/100. The airports section above carries the live status and delay window at both ends.
Morning or evening flight on MDW–ORD?
Operators schedule evening departures around 18:25 from MDW. Earlier flights typically land before destination-airport delays accumulate later in the day; check the ORD delay card to confirm conditions when you'd arrive.
How long is the flight from MDW to ORD?
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 MDW–ORD fly?
United Airlines runs the route with about 4 flights a week (mon, tue). Since one carrier owns the route, a single disruption tends to ripple through the day.