CLE → MDWCleveland to Chicago

live

Direct flights from Cleveland (CLE) to Chicago (MDW): 7 nonstop departures observed each week across 1 airline. 46% of the last 13 operated flights arrived within 15 minutes of schedule. The median arrival is 18 minutes late. No cancellations were recorded across the 13 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 22 October 2026 at 14:03 UTC.

Today, CLE → MDW

Thu 22 Oct · local times
  1. 08:20 WN1207Southwest Airlines Left 08:31 +11 Landed 08:28 −12
  2. · WN2068Southwest Airlines On schedule MDW 20:35scheduled

Checked CLE board 10:03 · MDW board 08:54

CLE Cleveland smooth · +0
MDW Chicago smooth · +0
492 km · ~1h 08m est.
dep bank 08:20–20:207x weekly
Runs rough · 1 airline · 7x weekly · nonstop
46% on time

of the last 13 operated CLE → MDW flights arrived within 15 minutes

Median arrival delay is +18 min. 0 of 13 tracked legs cancelled in the sample. Will a delayed flight be cancelled? →

Median arrival+18 minacross the last 13 operated legs
Flight time~1h 08mestimated from route distance
Weekly departures7x1 direct airline on the leg
Cancelled0.0%recent route rate · 0 of 13

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 AirlinesWN60% on time

Flights WN1207 varies Mo Th Fr Sa Su · WN3654 08:35 Tu We · WN833 13:25 Su · WN1209 varies Mo Tu We Th Fr

History

operated legs · board outcomes
10-22WN1207dep +11 → arr−12
10-21WN1209dep +14 → arr−6
10-21WN1211dep +8 → arr−13
10-21WN3654dep +42 → arr+18
10-20VJA302departed+634
10-20WN1209dep +6 → arr−16
10-20WN1211dep +11 → arr−7
10-20WN3654dep +75 → arr+23
10-19ERY106dep +0 → arr+22
10-19LXJ409dep +43 → arr+34
10-19WN1207departed+29
10-19WN1209departed+25
10-19WN2068departed+15

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 +0 min smooth 🌤 clear · SW 3 kt Full CLE delay board →
MDWChicago +0 min smooth 🌤 clear · NW 3 kt Full MDW delay board →

Weather lens

Current conditions put the pressure at CLE and MDW: 42% odds of a 15+ minute delay and around +9 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. 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 CLE–MDW?

Operators schedule morning departures around 08:35 and 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 20 flights a week (daily). Since one carrier owns the route, a single disruption tends to ripple through the day.