Route reliability record
CLE→MDW
Cleveland to Chicago
- Flights
- 1,115
- Period
- September 2025 to August 2026
- Distance
- 307 mi
- Carriers
- 1
This route lands a B, 4 points better than the national rate of 77.3%. About one flight in five arrives 15 minutes late or worse, and those flights are late by roughly 50 minutes on average. That rests on 1,115 CLE to MDW flights, with a median arrival 5 minutes early.
Best time to fly CLE to MDW: a 5am–8am departure, ideally on a Wednesday. Flights in that window arrived on time 89.7% of the time and Wednesday flights 88.4%, against 80.9% for the route overall.
The US average over the same twelve months is 77.3%, so there is little to separate this route from the country as a whole. The variation that matters here is internal: which carrier, and what time of day.
Key figures
On time
80.9%
Arrivals under 15 minutes late, of 1,100 completed flights
Avg delay
51 min
Across delayed arrivals only, not all flights
Cancelled
1.08%
National rate is 1.89%
Best carrier
Southwest
80.9% on time across 1,115 flights
These figures cover 1,115 flights between September 2025 and August 2026. The median arrival is 5 minutes early, which is the part an average hides: most flights here are fine, and the on-time rate is decided by a tail of badly late ones. On-time means under 15 minutes late, the DOT's own threshold.
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Carrier by carrier
Which airline is most reliable on CLE to MDW
Only one carrier clears this site's 365-flight floor here, so there is no comparison to draw. The table below is the full picture.
| Airline | Flights | On time | Avg delay | Cancelled | Grade |
|---|---|---|---|---|---|
| Southwest Airlines | 1,115 | 80.9% | 51 min | 1.08% | B |
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Best ways to make this trip
The most reliable ways to fly Cleveland to Chicago
Every airline on this route and on the routes between nearby airports, ranked by how often a scheduled flight actually operated and arrived on time. 4 of the top 5 use a different airport at one end.
| Option | Airline | Success | On time | Cancelled | Best departure | Most punctual flight |
|---|---|---|---|---|---|---|
| 1. CLE → MDWCleveland to Chicago | Southwest Airlines | 80.0% | 80.9% | 1.08% | 5am–8am, Wed | — |
| 2. CLE → ORDCleveland to Chicago | United Airlines | 74.5% | 75.6% | 1.47% | 5am–8am, Sat | UA 609 11:00 |
| 3. CLE → ORDCleveland to Chicago | American Airlines | 72.3% | 75.0% | 3.54% | 5am–8am, Sat | — |
| 4. CLE → ORDCleveland to Chicago | Republic Airways | 71.8% | 76.9% | 6.64% | 5am–8am, Tue | — |
| 5. CLE → ORDCleveland to Chicago | Envoy Air | 71.7% | 74.9% | 4.33% | 5am–8am, Sat | — |
Success is the share of scheduled flights that operated and arrived less than 15 minutes late, so a cancelled flight counts against it. “(route)” means the best time comes from every carrier on the route rather than this airline alone.
Departure window
The best time of day to leave
Departure time matters more here than the choice of carrier. The gap between the best and worst window is 20 points, against half a point between the best and worst carrier.
- 5am–8am196 flights89.7%
- 8am–11am169 flights81.1%
- 11am–2pm177 flights86.9%
- 2pm–5pm264 flights81.2%
- 5pm–8pm159 flights72.8%
- 8pm–5am150 flights70.1%
Scale runs 60% to 95%.
Book the early departure. Flights leaving between 5am–8am arrive on time 89.7% of the time, against 70.1% for the overnight window. That is 20 points of difference for no extra money, and it comes from the same aircraft having had no earlier flight to fall behind on. The 2pm–5pm window is the busiest, with 264 flights scheduled in it.
Explore
Filter CLE to MDW by airline, time, month and day
Pick a breakdown and a carrier. The dashed mark on each row is the same slice for every US flight.
On CLE to MDW, the best departure window is 5am–8am at 89.7% on time and the worst is 8pm–5am at 70.1%, a wide gap of 19.6 points. All US flights leaving 5am–8am ran 89.3%.
- 5–8am89.7%
- 8–11am81.1%
- 11am–2pm86.9%
- 2–5pm81.2%
- 5–8pm72.8%
- 8pm–5am70.1%
best all US flightsScale 60% to 95%.
Across the year
When delays peak on this route
This route's year swings by 26 points from best month to worst, which is wide. An annual average tells you very little about the week you are actually flying, so read the strip rather than the headline if your dates are fixed.
August is the worst month at 62.3% on time, 26 points below September, the best at 88.0%. Summer afternoon convection and peak-season schedules land on the same weeks every year, so this is a pattern you can book around rather than a run of bad luck. July was the busiest month here, with 115 flights.
Across the week, Wednesday is the strongest day at 88.4% on time and Monday the weakest at 70.8%, a spread of 18 points.
Delay causes
Why this route gets delayed
Late-arriving aircraft accounts for 44% of the 11,000 delay minutes carriers reported here, and the remaining four split what is left.
- 44%Late-arriving aircraft
- 27%National Airspace System
- 22%Carrier
- 7%Extreme weather
44% of delay minutes trace back to a late-arriving aircraft, meaning the plane was already behind before it got here. Across 11,000 reported delay minutes here, that single category outweighs weather by 6 to one. The split is drawn from 10,748 reported delay minutes.
The practical consequence: the 5am–8am departure is the one that starts clean. Its aircraft has no earlier leg to be late from, which is exactly why that window shows 89.7% on time here.
Cancellations sit at 1.08% against a national 1.89%, which is ordinary. Diversions add another 0.27%.
Connections and stage length
What a delay here actually costs
Badly late arrivals are rare here: only 4.6% land an hour or more behind schedule, against 8.3% nationally. Connections built on this flight are about as safe as US domestic connections get, though a cancelled flight still ignores every layover you give it.
At 307 miles this is a short hop, and stage length matters more than it looks. A flight this short spends under two hours in the air, which leaves almost nothing to claw back a late pushback with. Delay here is decided on the ground, in the turn, which is why the 5am–8am window matters as much as it does.
The return leg runs 79.6% on time across 1,115 flights, within about a point of this direction. The two legs are scored separately because they usually differ; on this city pair they happen not to.
The sample behind these figures is 1,115 flights, enough that the headline rate is stable to within roughly a point. The hour-block and month splits divide that further, so read the thinner bars with more caution than the headline.
Work out the risk of missing a connection in MDW after this flight
What to do with this
Booking this route
Put together: the calendar is the biggest lever here, not the carrier or the hour. September runs 88.0% on time and August 62.3%, a swing of 26 points. If the dates move at all, move them out of August before you think about anything else. 1,100 completed flights over 12 months sit behind that.
Common questions
CLE to MDW questions
How often is CLE to MDW delayed?
About one flight in five arrives at least 15 minutes late, which is the Department of Transportation's definition of a delayed arrival. That works out to 19.1% of the 1,115 flights in this analysis, against 22.7% nationally. Delayed flights are late by roughly 50 minutes on average.
How reliable is CLE to MDW compared with the rest of the country?
80.9% of flights arrive on time here against a national 77.3%, a difference of 4 points in its favour. That is worth a B on this site's grading scale.
What time of day has the fewest delays on CLE to MDW?
The 5am–8am departure window is the strongest at 89.7% on time. The 8pm–5am window is the weakest at 70.1%, 20 points behind. Later departures inherit delays from earlier flights the same aircraft has already flown, which is why the curve slopes the way it does.
How bad are August delays on CLE to MDW?
August is the weakest month at 62.3% on time, compared with 88.0% in September. Across the year that is 26 points between the best and worst months. Moving flexible dates out of that month is one of the few things that reliably helps.
Related
Where to go next
- MDW to CLE — the return legseparate record
- Cleveland Hopkins International (CLE) delay statistics
- Chicago Midway International (MDW) delay statistics
- CLE to ORD, a related route74.5%
- ATL to MDW, a related route75.2%
- CLE to ATL, a related route84.6%
- Southwest Airlines on-time record80.9%
- Why the first flight of the morning is statistically safest
- The best time of day to fly, according to 7.05 million flight records
Direction matters. CLE to MDW and MDW to CLE are scored separately because they are separate operations, with different departure banks and different aircraft. Compare the return leg.
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Source: US DOT Bureau of Transportation Statistics, on-time performance data, September 2025 to August 2026. Last updated ; recomputed monthly. How this data is collected.