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DelayAtlas

Route reliability record

ORD→SJU

Chicago to San Juan

Flights
1,390
Period
September 2025 to August 2026
Distance
2,072 mi
Carriers
4
CGRADE

This route sits in the middle of the pack with a C. Close to three flights in four arrive on time by the DOT's definition, 4 points worse than the national rate of 77.3%. The late ones land a little over an hour behind schedule. That rests on 1,390 ORD to SJU flights, of which United Airlines flew 657 at 79.2% on time.

Best time to fly ORD to SJU: a 2pm–5pm departure, ideally on a Wednesday. Flights in that window arrived on time 78.8% of the time and Wednesday flights 78.4%, against 73.2% for the route overall.

The national on-time rate over the same period is 77.3%, so this route runs 4 points behind the country as a whole. Across a thousand flights that is about 41 extra late arrivals.

Key figures

On time

73.2%

Arrivals under 15 minutes late, of 1,356 completed flights

Avg delay

70 min

Across delayed arrivals only, not all flights

Cancelled

2.23%

National rate is 1.89%

Best carrier

United

79.2% on time across 657 flights

These figures cover 1,390 flights between September 2025 and August 2026. Beyond the headline rate, 9.4% of arrivals land a full hour or more behind schedule, against 8.3% nationally.

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Carrier by carrier

Which airline is most reliable on ORD to SJU

The choice of carrier is not cosmetic here. United Airlines arrives on time 79.2% of the time; American Airlines manages 71.2%. Sample sizes sit next to every figure, because a two-point gap across 429 flights means less than a ten-point one.

On-time performance by carrier on ORD to SJU
AirlineFlightsOn timeAvg delayCancelledGrade
United Airlines65779.2%52 min0.30%B+
American Airlines42971.2%64 min1.63%C
Frontier Airlinesthin sample7266.7%189 min4.17%C−
Spirit Airlinesthin sample23260.8%76 min8.19%D−

United leads American by 8 points. Real, but small enough that a better departure time on the weaker carrier can outweigh it.

Flight by flight

Flights on ORD to SJU

The flight numbers below flew this route at least 250 times in the period, busiest first. Each has its own record, with its schedule and delay causes.

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Best ways to make this trip

The most reliable ways to fly Chicago to San Juan

Every airline on this route, ranked by how often a scheduled flight actually operated and arrived on time, with its best departure time and most punctual flight number. No nearby airport pair beat these.

Most reliable ways to fly from ORD to SJU
OptionAirlineSuccessOn timeCancelledBest departureMost punctual flight
1. ORD → SJUChicago to San JuanUnited Airlines79.0%79.2%0.30%2pm–5pm, WedUA 695 14:20
2. ORD → SJUChicago to San JuanAmerican Airlines70.0%71.2%1.63%8pm–5am, Wed—

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.

Plan this trip by month, day and time

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 8 points between the best and worst carrier.

  • 5am–8am41 flights70.3%
  • 8am–11am626 flights77.9%
  • 11am–2pm116 flights59.5%
  • 2pm–5pm328 flights78.8%
  • 5pm–8pm103 flights57.8%
  • 8pm–5am176 flights64.0%

Scale runs 50% to 85%.

The 5pm–8pm window is where this operation falls apart: 57.8% on time, against 78.8% for the 2pm–5pm 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 8am–11am window is the busiest, with 626 flights scheduled in it.

Explore

Filter ORD to SJU 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 ORD to SJU, the best departure window is 2pm–5pm at 78.8% on time and the worst is 5pm–8pm at 57.8%, a wide gap of 21.0 points. All US flights leaving 2pm–5pm ran 71.9%.

  • 5–8am70.3%
  • 8–11am77.9%
  • 11am–2pm59.5%
  • 2–5pm78.8%
  • 5–8pm57.8%
  • 8pm–5am64.0%

best all US flightsScale 50% to 95%.

Across the year

When delays peak on this route

This route's year swings by 28 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.

On-time rate by calendar month70J87F59M78A83M68J71J65A78S80O74N73D
Darker means more delays. Figures are on-time percentages.February best, March worst

Delays peak in March, when the on-time rate falls to 59.4%. February is the strongest month at 87.1%. Moving a flexible trip across that boundary buys 28 points. March was the busiest month here, with 179 flights.

Across the week, Wednesday is the strongest day at 78.4% on time and Monday the weakest at 67.5%, a spread of 11 points.

On-time rate by day of the week67.5Mon75.4Tue78.4Wed75.5Thu73.8Fri71.7Sat70.9Sun
Monday: 67.5 percent on time. Tuesday: 75.4 percent on time. Wednesday: 78.4 percent on time. Thursday: 75.5 percent on time. Friday: 73.8 percent on time. Saturday: 71.7 percent on time. Sunday: 70.9 percent on time

Delay causes

Why this route gets delayed

Carriers report a reason for every delay minute they cause, in five DOT categories. The split below is by minutes, not by number of flights, so a handful of very long weather delays weighs as much as many short ones. It covers 25,000 reported delay minutes.

  • Carrier
    36%
  • Late-arriving aircraft
    31%
  • National Airspace System
    25%
  • Extreme weather
    9%
  • Security
    0%

The largest share of delay minutes, 36%, falls under carrier control: crew scheduling, maintenance, fuelling, baggage. It accounts for 9,134 of the 25,000 delay minutes reported here. The split is drawn from 25,444 reported delay minutes.

Cancellations sit at 2.23% against a national 1.89%, which is ordinary. Diversions add another 0.22%.

Connections and stage length

What a delay here actually costs

9.4% of arrivals land a full hour or more behind schedule, against 8.3% nationally. Ninety minutes is the honest minimum for a connection here, and two hours if the onward flight is on a separate ticket.

At 2,072 miles this is transcontinental flying, and long routes get a quiet structural advantage. Scheduled block time on a flight this length carries more padding in absolute minutes, so a twenty-minute late departure often still becomes an on-time arrival. Read the on-time rate here as slightly flattering next to a short-haul route with the same operational quality.

The return leg is a different operation and performs like one: it runs 78.3% on time across 1,383 flights, 5 points above 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 5 points of difference.

The sample behind these figures is 1,390 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 SJU 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. February runs 87.1% on time and March 59.4%, a swing of 28 points. If the dates move at all, move them out of March before you think about anything else. 1,356 completed flights over 12 months sit behind that.

Common questions

ORD to SJU questions

How often is ORD to SJU 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 26.8% of the 1,390 flights in this analysis, against 22.7% nationally. Delayed flights are late by a little over an hour on average.

Which airline is most reliable on ORD to SJU?

United Airlines leads at 79.2% on time across 657 flights. American Airlines is at the other end on 71.2%, a gap of 8 points. Sample size matters as much as the percentage: a rate built from a few hundred flights moves around far more than one built from ten thousand.

What time of day has the fewest delays on ORD to SJU?

The 2pm–5pm departure window is the strongest at 78.8% on time. The 5pm–8pm window is the weakest at 57.8%, 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 ORD to SJU?

March is the weakest month at 59.4% on time, compared with 87.1% in February. Across the year that is 28 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

Direction matters. ORD to SJU and SJU to ORD 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.