Route reliability record
MSY→MDW
New Orleans to Chicago
- Flights
- 1,018
- Period
- July 2025 to June 2026
- Distance
- 825 mi
- Carriers
- 1
This route lands a B, level with the national rate of 77.6%. Roughly one flight in four arrives 15 minutes late or worse, and those flights are late by roughly 55 minutes on average. That is a workable record, not a spotless one. That rests on 1,018 MSY to MDW flights, with a median arrival 1 minute early.
Best time to fly MSY to MDW: a 5am–8am departure, ideally on a Tuesday. Flights in that window arrived on time 92.9% of the time and Tuesday flights 86.5%, against 77.1% for the route overall.
The US average over the same twelve months is 77.6%, 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
77.1%
Arrivals under 15 minutes late, of 1,000 completed flights
Avg delay
53 min
Across delayed arrivals only, not all flights
Cancelled
1.08%
National rate is 1.81%
Best carrier
Southwest
77.1% on time across 1,018 flights
These figures cover 1,018 flights between July 2025 and June 2026. On-time means an arrival less than 15 minutes after the scheduled gate time, the same threshold the Department of Transportation uses in its own reports. Cancelled and diverted flights are excluded from the on-time rate and counted separately, which is why the cancellation column matters on its own.
Carrier by carrier
Which airline is most reliable on MSY 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 | 1,018 | 77.1% | 53 min | 1.08% | B |
Best ways to make this trip
The most reliable ways to fly New Orleans 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. 3 of the top 4 use a different airport at one end.
| Option | Airline | Success | On time | Cancelled | Best departure | Most punctual flight |
|---|---|---|---|---|---|---|
| 1. MSY → ORDNew Orleans to Chicago | United Airlines | 81.3% | 82.3% | 1.19% | 5am–8am, Thu | — |
| 2. MSY → ORDNew Orleans to Chicago | Envoy Air | 80.7% | 82.1% | 1.72% | 5am–8am, Tue | — |
| 3. MSY → MDWNew Orleans to Chicago | Southwest Airlines | 76.3% | 77.1% | 1.08% | 5am–8am, Tue | — |
| 4. MSY → ORDNew Orleans to Chicago | American Airlines | 68.7% | 70.3% | 2.25% | 5am–8am, Tue | — |
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 40 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–8am345 flights92.9%
- 8am–11am86 flights91.8%
- 11am–2pm159 flights82.1%
- 2pm–5pm197 flights67.7%
- 5pm–8pm222 flights52.5%
- 8pm–5am9 flights—
Scale runs 45% to 100%. Rows with fewer than 30 flights show a dash.
The 5pm–8pm window is where this operation falls apart: 52.5% on time, against 92.9% for the 5am–8am slot. By evening the aircraft flying these rotations have absorbed a full day of small delays and there is no slack left to recover in. The 5am–8am window is the busiest, with 345 flights scheduled in it.
Across the year
When delays peak on this route
This route's year swings by 33 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.
Delays peak in March, when the on-time rate falls to 59.1%. February is the strongest month at 92.6%. Moving a flexible trip across that boundary buys 33 points. July was the busiest month here, with 97 flights.
Across the week, Tuesday is the strongest day at 86.5% on time and Friday the weakest at 70.1%. 16 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 57% of the 12,000 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.
- 57%Late-arriving aircraft
- 25%Carrier
- 12%National Airspace System
- 6%Extreme weather
- 1%Security
57% 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 12,000 reported delay minutes here, that single category outweighs weather by 10 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 12,177 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 92.9% on time here.
Cancellations sit at 1.08% against a national 1.81%, which is ordinary. Diversions add another 0.69%.
Connections and stage length
What a delay here actually costs
6.2% of arrivals land an hour or more late, close to the national 8.1%. That is the figure that decides a connection, and it says a 60 to 75 minute layover is reasonable here while anything under 45 minutes is a bet. Most delays on this route last roughly 55 minutes, which a normal layover absorbs.
The 825 miles between these two airports put this in the middle of the US network, around two and a half to three hours of block time. That is enough cruise to absorb a ten-minute late pushback and not enough to absorb thirty. It is also long enough that the aircraft usually flies three or four legs a day rather than six, which slows how fast delay compounds.
The return leg is a different operation and performs like one: it runs 74.1% on time across 1,017 flights, 3 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 3 points of difference.
One caution: this is a thin sample. 1,018 flights over twelve months is enough to clear this site's floor but not enough to pin the rate down tightly, and a single bad week moves it by more than a point. Treat the grade as a rough reading.
Work out the risk of missing a connection in MDW after this flight
What to do with this
Booking this route
Put together: treat all of this as provisional. 1,018 flights over twelve months is enough to clear this site's floor and not enough to be confident to better than a couple of points. The 77.1% headline is the most reliable number on the page; the hour and month splits below it are built on a few dozen flights each. 1,000 completed flights over 12 months sit behind that.
Common questions
MSY to MDW questions
How often is MSY to MDW delayed?
Roughly one flight in four arrives at least 15 minutes late, which is the Department of Transportation's definition of a delayed arrival. That works out to 22.9% of the 1,018 flights in this analysis, against 22.4% nationally. Delayed flights are late by roughly 55 minutes on average.
How reliable is MSY to MDW compared with the rest of the country?
77.1% of flights arrive on time here against a national 77.6%, a difference of half a point against it. That is worth a B on this site's grading scale.
What time of day has the fewest delays on MSY to MDW?
The 5am–8am departure window is the strongest at 92.9% on time. The 5pm–8pm window is the weakest at 52.5%, 40 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 MSY to MDW?
March is the weakest month at 59.1% on time, compared with 92.6% in February. Across the year that is 33 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 MSY — the return legseparate record
- Louis Armstrong New Orleans International (MSY) delay statistics
- Chicago Midway International (MDW) delay statistics
- MSY to ATL, a related route83.3%
- ATL to MDW, a related route76.3%
- MSY to IAH, a related route82.2%
- Southwest Airlines on-time record77.1%
- 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. MSY to MDW and MDW to MSY 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.