AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in September 2026 (see full year).

Return flights

01 Sep - 09 Sep	Spirit Airlines
22 Sep - 22 Sep	United	direct
21 Sep - 24 Sep	United	direct
21 Sep - 25 Sep	United	direct
22 Sep - 25 Sep	United	direct
17 Sep - 17 Sep	United
24 Sep - 28 Sep	United
01 Sep - 09 Sep	United	direct
16 Sep - 20 Sep	United
17 Sep - 20 Sep	United

Also check the deals for one-way flights from Chicago to San Juan in September.

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Cheapest return flights from Chicago to San Juan in September from 314€

Return flights