Nonstop flights from Chicago to San Juan

4 airlines fly from 2 Chicago airports (ORD and MDW) to San Juan (SJU), with up to 4 flights a day.

ORDSJU

Routes

2 airport pairs

ORD to SJUChicago O'Hare to Luis Munoz Marin3 a day
MDW to SJUChicago Midway to Luis Munoz Marin1 a week

When they leave

Chicago time

12:44a5:20pFirst departure 12:44 AM, last 5:20 PM

One overnight flight at 12:44 AM, then two in the morning, 8:15 AM to 8:55 AM, then one evening flight at 5:20 PM.

Every flight

Earliest first

12:44 AM→6:44 AMORD to SJUFrontier AirlinesResumes Nov 20Airbus A321neoDaily
8:15 AM→3:00 PMMDW to SJUSouthwest AirlinesResumes Nov 7Boeing 737 MAX 8Sat
8:55 AM→2:44 PMORD to SJUUnited AirlinesAirbus A321neoDaily
5:20 PM→11:15 PMORD to SJUAmerican AirlinesBoeing 737Daily

Schedules last checked Sep 22, 2026. Times are local.

Flying from Chicago to San Juan

American Airlines flies daily on the Boeing 737. Frontier Airlines flies daily on the Airbus A321neo. United Airlines flies daily on the Airbus A321neo. Southwest Airlines flies on Saturdays with the Boeing 737 MAX 8.

Flights run every day of the week, 4 on Saturdays and 3 on the other days. The first arrival in San Juan is at 6:44 AM and the last at 11:15 PM.

ORD to SJU is the busiest airport pair, with 21 flights a week, then MDW to SJU with 1.

On ORD to SJU, Frontier Airlines is back on Nov 20. On MDW to SJU, Southwest Airlines is back on Nov 7.

Flying back, San Juan to Chicago has 22 nonstop flights a week.

Return flights

San Juan to ChicagoView

Find the cheapest day to fly from Chicago to San Juan.

Schedules as of Oct 9, 2026.