Cheapest return flights from Chicago to San Juan in September from $218

AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in September 2025 (see full year).

Return flights

15 Sep - 20 Sep Spirit Airlines
13 Sep - 20 Sep Spirit Airlines
15 Sep - 25 Sep Spirit Airlines
06 Sep - 20 Sep Spirit Airlines
20 Sep - 26 Sep Spirit Airlines
20 Sep - 28 Sep Spirit Airlines
20 Sep - 09 Oct Spirit Airlines
20 Sep - 06 Oct Spirit Airlines
20 Sep - 07 Oct Spirit Airlines
20 Sep - 10 Oct Spirit Airlines
19 Sep - 20 Sep Spirit Airlines
20 Sep - 29 Sep Spirit Airlines
14 Sep - 20 Sep Spirit Airlines
20 Sep - 03 Oct Spirit Airlines
20 Sep - 02 Oct Spirit Airlines
07 Sep - 20 Sep Spirit Airlines
27 Sep - 03 Oct Spirit Airlines
27 Sep - 14 Oct Spirit Airlines
27 Sep - 02 Oct Spirit Airlines
27 Sep - 16 Oct Spirit Airlines

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

Skyscanner

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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