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

Return flights

03 Sep - 08 Sep	Spirit Airlines	direct
21 Sep - 25 Sep	United	direct
24 Sep - 24 Sep	American Airlines
29 Sep - 29 Sep	Delta
24 Sep - 01 Oct	United
16 Sep - 20 Sep	American Airlines
11 Sep - 20 Sep	American Airlines
23 Sep - 27 Sep	American Airlines
29 Sep - 29 Sep	United	direct

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.

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Cheapest return flights from Chicago to San Juan in September from $327

Return flights