ORD to EYW flight delays
Chicago, IL (ORD) Key West, FL (EYW) · 1,251 miles
717 flights · January 2025 – August 2026 · US Bureau of Transportation Statistics
80.54%
Arrived on time
Within 15 minutes of schedule
1.26%
Cancelled
Share of scheduled flights
64 min
When late, late by
Average across delayed arrivals
13 min
Delay per flight
Averaged over every flight flown
What the record says about this route
The season swings this route hard. In May it ran 26.8 points more punctual than in December — a difference bigger than the one between the best and worst airlines on most routes. If the date is flexible, it is worth more than the carrier.
The two directions do not behave alike. EYW to ORD arrives on time 13.1 points less often than the outbound. Delay accumulates through the flying day, so whichever direction is scheduled later tends to carry the worse record — which is an argument for booking the morning departure if the choice exists.
This route does better than its own airport. Departures from ORD overall run 7.6 points less punctual than this particular one — so whatever congestion ORD has, this route is largely escaping it.
The 3 airlines here are separated by under 5 points — close enough to call a tie. Choose on price and departure time.
Which airline should you fly on this route?
Over January 2025 – August 2026, Envoy Air arrived on time most often on ORD to EYW. United Airlines was late most often. Flights ran closest to schedule in July and worst in December.
Every airline on ORD to EYW
Ranked by how many flights each one operated. A carrier with fewer than 100 flights in the period is listed but not graded.
| Airline | Flights | On time | Cancelled | Avg delay | Grade |
|---|---|---|---|---|---|
| Envoy Air | 407 | 82.04% | 1.23% | 63 min | B |
| Republic Airways | 172 | 79.64% | 1.74% | 55 min | C |
| United Airlines | 138 | 77.21% | 0.72% | 75 min | C |
Month by month
Share of flights that arrived within 15 minutes of schedule, by month flown.
The return leg
EYW to ORD Key West back to Chicago 67.44% on time FOther routes from Chicago
Common questions
Are flights from Chicago to Key West usually delayed?
80.54% of flights on the ORD to EYW route arrived within 15 minutes of schedule, so roughly 2 in every ten arrived late. That is better than the average route in this record.
Which airline is most on time from Chicago to Key West?
Envoy Air, at 82.04% on time across 407 flights. The least punctual on the route was United Airlines at 77.21%.
How often are ORD to EYW flights cancelled?
1.26% of scheduled flights did not operate — about 13 in every thousand. That is in the normal range.
What is the best month to fly Chicago to Key West?
May, when 92.7% of flights arrived on time. The worst was December at 65.9%.
When ORD to EYW flights are late, how late are they?
About 64 minutes on average across the flights that arrived more than 15 minutes behind schedule.
What these figures do and do not tell you
Everything on this page is counted from the flights that actually operated on ORD to EYW during January 2025 – August 2026, as reported by the airlines to the US Bureau of Transportation Statistics. "On time" is the federal definition: arriving at the gate within 15 minutes of the scheduled time.
A route's record is a description of the past, not a forecast. Weather, air traffic control and the aircraft's earlier flights that day drive most delays, and none of them are predictable from a historical rate. What the record does tell you is whether this route runs late more often than others, and which carrier on it has the better history — which is the part you can actually act on when you book.
Cancellations are counted separately from delays because they are a different problem for a traveller: a late flight still gets you there. How the grade is calculated →