Chicago to San Juan (ORD-SJU): nonstop upgrade & award space

United Airlines, American Airlines, and Frontier Airlines fly nonstop between Chicago (ORD) and San Juan (SJU), roughly 15 times a week. United Airlines carries most of this long-haul schedule, so one carrier's release pattern decides when premium space appears, and it is rarely all at once. 2LNR tracks confirmed upgrade and award space on American Airlines, on every ORD to SJU departure, so you know which flights have space before you book.

Schedule last confirmed . Departure times come from 2LNR's schedule data; confirm with the airline before you book.

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15
Nonstop flights a week
2,074 mi
Nonstop distance
Free
To get started

Chicago to San Juan flight schedule

Scheduled nonstop departures for ORD to SJU, last checked against our schedule feed on September 6, 2026. Airlines retime and cancel flights, so confirm with the airline before you book.

Schedule data dated .

Scheduled nonstop departures from Chicago (ORD) to San Juan (SJU)
Date Flight Airline Departs ORD Arrives SJU Duration Aircraft
UA 1996United Airlines08:5514:444h 49m32Q
UA 695United Airlines14:3820:344h 56m32Q
UA 1996United Airlines08:5514:444h 49m32Q
UA 695United Airlines14:3820:344h 56m32Q
UA 1996United Airlines08:5514:444h 49m32Q
UA 695United Airlines14:3820:344h 56m32Q
UA 1996United Airlines08:5514:444h 49m32Q
UA 695United Airlines14:3820:344h 56m32Q
UA 1996United Airlines08:5514:444h 49m32Q
UA 695United Airlines14:3820:344h 56m32Q
UA 1996United Airlines08:5514:444h 49m32Q
UA 695United Airlines14:3820:344h 56m32Q
UA 1996United Airlines08:5514:444h 49m32Q
UA 695United Airlines14:3820:344h 56m32Q

Showing all 14 scheduled ORD to SJU departures across the next 7 days with service. Later dates are on the interactive map.

Departure and arrival times are local at their own airport, so an arrival can fall on a different local date than the departure; the duration column is the true elapsed flying time. A dash means the airline has not filed that value in the schedule data we hold. Aircraft are IATA equipment codes as filed, and can change up to departure.

See every ORD to SJU date on the interactive map

Confirmed upgrade & award space on ORD to SJU departures

2LNR tracks confirmed upgrade and award space on American Airlines, segment by segment and date by date. Open the calendar for Chicago to San Juan to see which departures have space, the next 14 days free on every product and the full horizon on Pro.

See real availability

Confirmed upgrade and award seats on each ORD to SJU departure, checked against live inventory so you know what is open before you book.

Set an alert

Premium inventory turns over fast. Watch this route and 2LNR notifies you when space appears on a date you are tracking.

Plan on the map

See ORD to SJU on the interactive route map, with schedules, connections, and route statistics.

Airlines flying Chicago to San Juan nonstop

Carriers operating ORD to SJU nonstop in the current schedule. 2LNR tracks confirmed upgrade and award space on each of them.

See ORD to SJU on the interactive map →

Frequently asked questions about ORD to SJU

How far is San Juan from Chicago?
ORD to SJU covers about 2,074 miles nonstop. Flight times vary by aircraft and season; the schedule table on this page lists each scheduled departure with its own times.
Which airlines fly nonstop from ORD to SJU?
United Airlines, American Airlines, and Frontier Airlines fly the route nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from ORD to SJU?
About 15 nonstop flights a week run between Chicago and San Juan in the current schedule, operated by United Airlines, American Airlines, and Frontier Airlines. Frequency shifts by season, and the schedule table on this page shows what is scheduled next.
What time do flights from ORD to SJU depart?
Scheduled ORD to SJU nonstops in the next 7 days with service leave between 08:55 and 14:38, local time at Chicago. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
How do I check upgrade or award availability on ORD to SJU?
Open the ORD to SJU route on the interactive map or the matrix to see confirmed upgrade and award space by date on American Airlines, the next 14 days free and the full horizon on Pro. On Pro you can also set an alert on the route and 2LNR notifies you when space opens.

Never miss ORD to SJU upgrade or award space

See what is open by date on this route, the next 14 days free on every product and the full horizon on Pro.

Get started free