Route reliability record
RSW→MDW
Fort Myers to Chicago
- Flights
- 1,161
- Period
- July 2025 to June 2026
- Distance
- 1,105 mi
- Carriers
- 1
This route sits in the middle of the pack with a B. Close to three flights in four arrive on time by the DOT's definition, 3 points worse than the national rate of 77.6%. The late ones land about an hour behind schedule. That rests on 1,161 RSW to MDW flights, with a median arrival 1 minute early.
Best time to fly RSW to MDW: a 5am–8am departure, ideally on a Wednesday. Flights in that window arrived on time 94.2% of the time and Wednesday flights 79.9%, against 75.0% 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
75.0%
Arrivals under 15 minutes late, of 1,137 completed flights
Avg delay
58 min
Across delayed arrivals only, not all flights
Cancelled
1.38%
National rate is 1.81%
Best carrier
Southwest
75.0% on time across 1,161 flights
These figures cover 1,161 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 RSW 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 | 1,161 | 75.0% | 58 min | 1.38% | B |
Best ways to make this trip
The most reliable ways to fly Fort Myers 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. RSW → ORDFort Myers to Chicago | United Airlines | 80.2% | 80.7% | 0.68% | 5am–8am, Thu | UA 2494 12:30 |
| 2. RSW → MDWFort Myers to Chicago | Southwest Airlines | 74.0% | 75.0% | 1.38% | 5am–8am, Wed | — |
| 3. RSW → ORDFort Myers to Chicago | American Airlines | 72.8% | 74.3% | 1.97% | 8am–11am, Tue | — |
| 4. RSW → ORDFort Myers to Chicago | Spirit Airlines | 66.4% | 70.1% | 5.21% | 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 42 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–8am331 flights94.2%
- 8am–11am113 flights81.8%
- 11am–2pm239 flights76.6%
- 2pm–5pm184 flights65.7%
- 5pm–8pm179 flights52.0%
- 8pm–5am115 flights60.4%
Scale runs 45% to 100%. Rows with fewer than 30 flights show a dash.
The 5pm–8pm window is where this operation falls apart: 52.0% on time, against 94.2% 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 331 flights scheduled in it.
Across the year
When delays peak on this route
This route's year swings by 30 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.
December is the weak month at 61.1% on time, against 91.3% in September. Winter delays cluster: a single storm system can account for most of a month's shortfall, so an average December hides both very good weeks and genuinely unflyable days. March was the busiest month here, with 163 flights.
Across the week, Wednesday is the strongest day at 79.9% on time and Sunday the weakest at 70.5%. 9 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 16,000 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
- 22%Carrier
- 16%National Airspace System
- 5%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 16,000 reported delay minutes here, that single category outweighs weather by 12 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 16,376 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 94.2% on time here.
Cancellations sit at 1.38% against a national 1.81%, which is ordinary. Diversions add another 0.69%.
Connections and stage length
What a delay here actually costs
7.7% 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 about an hour, which a normal layover absorbs.
The 1,105 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 runs 75.6% on time across 1,162 flights, within half 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 1,161 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 91.3% on time and December 61.1%, a swing of 30 points. If the dates move at all, move them out of December before you think about anything else. 1,137 completed flights over 12 months sit behind that.
Common questions
RSW to MDW questions
How often is RSW to MDW delayed?
About 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 25.0% of the 1,161 flights in this analysis, against 22.4% nationally. Delayed flights are late by about an hour on average.
How reliable is RSW to MDW compared with the rest of the country?
75.0% of flights arrive on time here against a national 77.6%, a difference of 3 points against it. That is worth a B on this site's grading scale.
What time of day has the fewest delays on RSW to MDW?
The 5am–8am departure window is the strongest at 94.2% on time. The 5pm–8pm window is the weakest at 52.0%, 42 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 December delays on RSW to MDW?
December is the weakest month at 61.1% on time, compared with 91.3% in September. Across the year that is 30 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 RSW — the return legseparate record
- Southwest Florida International (RSW) delay statistics
- Chicago Midway International (MDW) delay statistics
- RSW to ORD, a related route76.5%
- ATL to MDW, a related route76.3%
- RSW to ATL, a related route85.7%
- Southwest Airlines on-time record75.0%
- 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. RSW to MDW and MDW to RSW 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.