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

American Airlines, United Airlines, and Frontier Airlines fly nonstop between Chicago (ORD) and San Juan (SJU), roughly 21 times a week. The timetable below shows the nonstop scheduled at 4h 44m to 4h 56m for the 2,074 miles. 2LNR checks confirmed upgrade and award space on American Airlines flights on this route, so you can see which departures have space before you book.

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

Updated .

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21
Flights a week, 4-week average
4h 44m to 4h 56m
Scheduled flight time
2,074 mi
Nonstop distance
Free
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Chicago to San Juan flight schedule

Scheduled nonstop departures for ORD to SJU starting October 23, 2026, last checked against our schedule feed on October 18, 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
AA 1865American Airlines08:1314:034h 50mBoeing 737-800
UA 1996United Airlines08:5514:444h 49mAirbus A321neo family
AA 1865American Airlines08:1314:034h 50mBoeing 737-800
UA 1996United Airlines08:5514:444h 49mAirbus A321neo family
AA 1865American Airlines08:1314:034h 50mBoeing 737-800
UA 1996United Airlines08:5514:444h 49mAirbus A321neo family
UA 695United Airlines14:3820:344h 56mAirbus A321neo family
AA 1865American Airlines08:1314:034h 50mBoeing 737-800
UA 1996United Airlines08:5514:444h 49mAirbus A321neo family
UA 695United Airlines14:3820:344h 56mAirbus A321neo family
AA 1865American Airlines08:1314:034h 50mBoeing 737-800
UA 1996United Airlines08:5514:444h 49mAirbus A321neo family
UA 695United Airlines14:1620:004h 44mAirbus A321neo family
AA 1865American Airlines08:1314:034h 50mBoeing 737-800
UA 1996United Airlines08:5514:444h 49mAirbus A321neo family
UA 695United Airlines14:1620:004h 44mAirbus A321neo family
AA 1865American Airlines08:1314:034h 50mBoeing 737-800
UA 1996United Airlines08:5514:444h 49mAirbus A321neo family
UA 695United Airlines14:1620:004h 44mAirbus A321neo family

Showing all 19 scheduled ORD to SJU departures across 7 days with service, starting October 23, 2026. 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 hasn't filed that value in the schedule data we hold. Aircraft are the equipment the airline filed, named where the code pins down one type and shown as the family or the bare code where it doesn't. Swaps can happen up to departure.

See every ORD to SJU date on the interactive map

Aircraft on the Chicago to San Juan nonstop

In the schedule table on this page, United Airlines flies the Airbus A321neo family, and American Airlines flies the Boeing 737-800. Each linked aircraft page shows where that airline schedules it. Airlines can swap aircraft up to departure.

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.

American Airlines award space was open on none of the 14 Chicago to San Juan departure dates from October 19 to November 1 that 2LNR checked in the 7 days to October 19, 2026.

See real availability

Confirmed upgrade or award seats by date on the ORD to SJU departures 2LNR tracks, checked against live inventory so you know what's open before you book.

Set an alert

Premium inventory turns over fast. Watch this route on Pro and 2LNR notifies you when space appears on a date you're 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. Where 2LNR tracks the carrier, its departures show confirmed upgrade or award space by date.

See ORD to SJU on the interactive map →

Frequently asked questions about ORD to SJU

How long is the flight from Chicago (ORD) to San Juan (SJU)?
Scheduled flight times from Chicago (ORD) to San Juan (SJU) run from 4h 44m to 4h 56m across the departures in the schedule table on this page. The nonstop covers about 2,074 miles, and airlines adjust scheduled times by season, so confirm with the airline before you book.
Which airlines fly nonstop from ORD to SJU?
American Airlines, United Airlines, and Frontier Airlines fly ORD to SJU nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from ORD to SJU?
About 21 nonstop flights a week run between Chicago (ORD) and San Juan (SJU) in the current schedule, operated by American Airlines, United 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 08:13 and 14:38, local time at Chicago. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
Which flights operate ORD to SJU nonstop?
In the schedule table on this page, ORD to SJU nonstops fly as UA 695 and UA 1996 on United Airlines, and AA 1865 on American Airlines. The table lists each departure by date with its times 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.

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

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