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

American Airlines, United Airlines, and Frontier Airlines fly nonstop between San Juan (SJU) and Chicago (ORD), roughly 20 times a week. The timetable below shows the nonstop scheduled at 5h 9m to 5h 36m 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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20
Flights a week, 4-week average
5h 9m to 5h 36m
Scheduled flight time
2,074 mi
Nonstop distance
Free
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San Juan to Chicago flight schedule

Scheduled nonstop departures for SJU to ORD starting October 22, 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 San Juan (SJU) to Chicago (ORD)
Date Flight Airline Departs SJU Arrives ORD Duration Aircraft
AA 1865American Airlines14:5319:295h 36mBoeing 737-800
UA 2088United Airlines15:5620:055h 9mAirbus A321neo family
AA 1865American Airlines14:5319:295h 36mBoeing 737-800
UA 2088United Airlines15:5620:055h 9mAirbus A321neo family
AA 1865American Airlines14:5319:295h 36mBoeing 737-800
UA 2088United Airlines15:5620:055h 9mAirbus A321neo family
AA 1865American Airlines14:5319:295h 36mBoeing 737-800
UA 2088United Airlines15:5620:055h 9mAirbus A321neo family
UA 2089United Airlines07:4011:535h 13mAirbus A321neo family
AA 1865American Airlines14:5319:295h 36mBoeing 737-800
UA 2088United Airlines15:5620:055h 9mAirbus A321neo family
UA 2089United Airlines07:2511:475h 22mAirbus A321neo family
AA 1865American Airlines14:5319:295h 36mBoeing 737-800
UA 2088United Airlines15:5520:265h 31mAirbus A321neo family
UA 2089United Airlines07:2511:475h 22mAirbus A321neo family
AA 1865American Airlines14:5319:295h 36mBoeing 737-800
UA 2088United Airlines15:5520:265h 31mAirbus A321neo family

Showing all 17 scheduled SJU to ORD departures across 7 days with service, starting October 22, 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 SJU to ORD date on the interactive map

Aircraft on the San Juan to Chicago 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 SJU to ORD departures

2LNR tracks confirmed upgrade and award space on American Airlines, segment by segment and date by date. Open the calendar for San Juan to Chicago 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 3 of the 14 San Juan to Chicago 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 SJU to ORD 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 SJU to ORD on the interactive route map, with schedules, connections, and route statistics.

Airlines flying San Juan to Chicago nonstop

Carriers operating SJU to ORD nonstop in the current schedule. Where 2LNR tracks the carrier, its departures show confirmed upgrade or award space by date.

See SJU to ORD on the interactive map →

Frequently asked questions about SJU to ORD

How long is the flight from San Juan (SJU) to Chicago (ORD)?
Scheduled flight times from San Juan (SJU) to Chicago (ORD) run from 5h 9m to 5h 36m 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 SJU to ORD?
American Airlines, United Airlines, and Frontier Airlines fly SJU to ORD nonstop. 2LNR tracks confirmed upgrade and award space on American Airlines.
How many flights a week are there from SJU to ORD?
About 20 nonstop flights a week run between San Juan (SJU) and Chicago (ORD) 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 SJU to ORD depart?
Scheduled SJU to ORD nonstops in the next 7 days with service leave between 07:25 and 15:56, local time at San Juan. The schedule table on this page lists every departure by date, with its arrival time and aircraft.
Which flights operate SJU to ORD nonstop?
In the schedule table on this page, SJU to ORD nonstops fly as UA 2088 and UA 2089 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 SJU to ORD?
Open the SJU to ORD 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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