Route reliability record
CLE→MDW
Cleveland to Chicago
- Flights
- 1,109
- Period
- July 2025 to June 2026
- Distance
- 307 mi
- Carriers
- 1
This route lands a B+, 5 points better than the national rate of 77.6%. About one flight in six arrives 15 minutes late or worse, and those flights are late by about 55 minutes on average. That is a workable record, not a spotless one. That rests on 1,109 CLE to MDW flights, with a median arrival 6 minutes early.
Best time to fly CLE to MDW: a 5am–8am departure, ideally on a Wednesday. Flights in that window arrived on time 90.2% of the time and Wednesday flights 90.9%, against 82.6% for the route overall.
Set against the rest of the country, this route's record is 5 points better than the US average of 77.6%. That gap is worth roughly 50 fewer late arrivals for every thousand flights.
Key figures
On time
82.6%
Arrivals under 15 minutes late, of 1,096 completed flights
Avg delay
55 min
Across delayed arrivals only, not all flights
Cancelled
0.99%
National rate is 1.81%
Best carrier
Southwest
82.6% on time across 1,109 flights
These figures cover 1,109 flights between July 2025 and June 2026. The median arrival is 6 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.
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 | 1,109 | 82.6% | 55 min | 0.99% | B+ |
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 | 81.8% | 82.6% | 0.99% | 5am–8am, Wed | — |
| 2. CLE → ORDCleveland to Chicago | United Airlines | 75.9% | 77.0% | 1.47% | 5am–8am, Sat | UA 1673 18:00 |
| 3. CLE → ORDCleveland to Chicago | Republic Airways | 71.5% | 76.6% | 6.63% | 5am–8am, Tue | — |
| 4. CLE → ORDCleveland to Chicago | American Airlines | 70.4% | 74.1% | 5.00% | 5am–8am, Sat | — |
| 5. CLE → ORDCleveland to Chicago | Envoy Air | 70.3% | 73.7% | 4.55% | 11am–2pm, 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 21 points, against half a point between the best and worst carrier. Each bar is the on-time rate for flights scheduled inside that window.
- 5am–8am258 flights90.2%
- 8am–11am117 flights83.2%
- 11am–2pm195 flights84.6%
- 2pm–5pm250 flights81.5%
- 5pm–8pm145 flights81.2%
- 8pm–5am144 flights68.8%
Scale runs 60% to 95%. Rows with fewer than 30 flights show a dash.
Book the early departure. Flights leaving between 5am–8am arrive on time 90.2% of the time, against 68.8% for the overnight window. That is 21 points of difference for no extra money, and it comes from the same aircraft having had no earlier flight to fall behind on. The 5am–8am window is the busiest, with 258 flights scheduled in it.
Across the year
When delays peak on this route
This route's year swings by 15 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.
September is the best month on the calendar at 88.0% on time. Shoulder season thins the schedule and takes the summer weather with it, and the operation gets its margin back. July was the busiest month here, with 114 flights.
Across the week, Wednesday is the strongest day at 90.9% on time and Monday the weakest at 73.4%. 18 points is a smaller lever than departure hour, but it is free.
Delay causes
Why this route gets delayed
One category carries most of the weight here. Late-arriving aircraft accounts for 48% of the 10,000 delay minutes carriers reported, and the remaining four split what is left. The split is by minutes rather than by flights, so a few very long delays count for as much as many short ones.
- 48%Late-arriving aircraft
- 25%National Airspace System
- 20%Carrier
- 7%Extreme weather
48% of delay minutes trace back to a late-arriving aircraft, meaning the plane was already behind before it got here. That is a cascade, and cascades start small and grow through the day. Across 10,000 reported delay minutes here, that single category outweighs weather by 7 to one. It is the strongest argument for booking the first departure of the morning, when the aircraft has been sitting at the gate overnight with nothing to inherit. The split is drawn from 10,472 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 90.2% on time here.
Cancellations sit at 0.99% against a national 1.81%, which is ordinary. Diversions add another 0.18%.
Connections and stage length
What a delay here actually costs
Badly late arrivals are rare here: only 4.2% land an hour or more behind schedule, against 8.1% 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 is a different operation and performs like one: it runs 79.0% on time across 1,108 flights, 4 points below this direction. Departure banks, aircraft rotations and the congestion at each end all differ, so scoring the two directions together would average away a real 4 points of difference.
The sample behind these figures is 1,109 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 March 72.8%, a swing of 15 points. If the dates move at all, move them out of March before you think about anything else. 1,096 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 six arrives at least 15 minutes late, which is the Department of Transportation's definition of a delayed arrival. That works out to 17.4% of the 1,109 flights in this analysis, against 22.4% nationally. Delayed flights are late by about 55 minutes on average.
How reliable is CLE to MDW compared with the rest of the country?
82.6% of flights arrive on time here against a national 77.6%, a difference of 5 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 90.2% on time. The 8pm–5am window is the weakest at 68.8%, 21 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 March delays on CLE to MDW?
March is the weakest month at 72.8% on time, compared with 88.0% in September. Across the year that is 15 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 route74.6%
- ATL to MDW, a related route76.3%
- CLE to ATL, a related route85.4%
- Southwest Airlines on-time record82.6%
- Why the first flight of the morning is statistically safest
- The best time of day to fly, according to 7.04 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, July 2025 to June 2026. Last updated 15 September 2026; recomputed monthly. How this data is collected.