Nonstop flights from San Juan to Chicago
4 airlines fly from San Juan (SJU) to 2 Chicago airports (ORD and MDW), with up to 4 flights a day.
Routes
2 airport pairs- SJU to ORDLuis Munoz Marin to Chicago O'Hare3 a day
- SJU to MDWLuis Munoz Marin to Chicago Midway1 a week
When they leave
San Juan timeOne overnight flight at 12:55 AM, then two in the afternoon, 1:30 PM to 3:56 PM, then one evening flight at 7:14 PM.
Every flight
Earliest first
Schedules last checked Sep 22, 2026. Times are local.
Flying from San Juan to Chicago
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.
Flights run every day of the week, 4 on Saturdays and 3 on the other days. The first arrival in Chicago is at 5:00 AM and the last at 11:27 PM.
SJU to ORD is the busiest airport pair, with 21 flights a week, then SJU to MDW with 1.
On SJU to ORD, Frontier Airlines is back on Nov 20. On SJU to MDW, Southwest Airlines is back on Nov 7.
Flying back, Chicago to San Juan has 22 nonstop flights a week.
Return flights
Find the cheapest day to fly from San Juan to Chicago.
Schedules as of Oct 9, 2026.