CLE → MDWCleveland to Chicago

live

Direct flights from Cleveland (CLE) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 90% of the last 10 operated flights arrived within 15 minutes of schedule. The median arrival is on schedule. No cancellations were recorded across the 10 tracked flights. The nonstop covers 492 km, an estimated 1 hour 8 minutes in the air. Measured by Pro Flight Search from live flight boards at Cleveland and Chicago. Updated 9 September 2026 at 20:38 UTC.

CLE Cleveland busy · +15
MDW Chicago smooth · +0
492 km · ~1h 08m est.
dep bank 08:50–19:157x weekly
Runs reliable · 1 airline · 7x weekly · nonstop
90% on time

of the last 10 operated CLE → MDW flights arrived within 15 minutes

Median arrival delay is −1 min. 0 of 10 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival−1 minacross the last 10 operated legs
Flight time~1h 08mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 10

The week

scheduled departures · origin local time
06121824
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 days
Southwest AirlinesWN86% on time

Flights WN1142 varies daily · WN1354 varies Su · WN1654 12:50 Tu We · WN2097 13:50 Mo Th Fr

History

operated legs · board outcomes
09-09WN1142dep +14 → arr+4
09-09WN1654dep +21 → arr+2
09-081I417dep −6 → arr−17
09-08ERY707arrived−1
09-08LXJ583dep +102 → arr−2
09-08WN1142dep +11 → arr+2
09-08WN1654dep +11 → arr−11
09-08WN175dep +2 → arr−15
09-08WN491dep +1 → arr−22
09-07WN1142departed+21

Actual board outcomes rather than schedules, paired departure and arrival per flight and day.

Full board history, day by day →

Airports right now

live boards
CLECleveland +15 min busy 🌤 few clouds · SW 11 kt Full CLE delay board →
MDWChicago +0 min smooth 🌤 overcast · WSW 11 kt Full MDW delay board →

Weather lens

Current conditions put the pressure at CLE and MDW: 44% 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 →

How the Cleveland to Chicago route actually runs

Pro Flight Search records official board updates for nonstop CLE 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 — Cleveland (CLE) to Chicago (MDW) route reliability, measured from operated flights on official airport boards.

Canonical URL
https://proflightsearch.com/search-flights/CLE-MDW
How we measure this →

CLE to MDW questions

Is CLE–MDW running on time right now?

Smooth skies ahead. The departure side at CLE is the weaker end, route health score 90/100. The airports section above carries the live status and delay window at both ends.

Morning or evening flight on CLE–MDW?

Operators schedule evening departures around 17:25 from CLE. 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 CLE to MDW?

Great-circle distance is 492 km. With typical jet cruise speed plus taxi, climb and descent, expect roughly 65–72 min gate-to-gate on this route.

How often does CLE–MDW fly?

Southwest Airlines runs the route with about 26 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.