Cheapest return flights from Chicago to San Juan in September from 202€

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

Return flights

06 Sep - 13 Sep Frontier Airlines
06 Sep - 10 Sep Frontier Airlines
06 Sep - 18 Sep Spirit Airlines
20 Sep - 11 Oct Frontier Airlines
06 Sep - 26 Sep Spirit Airlines
07 Sep - 18 Sep Spirit Airlines
20 Sep - 26 Sep Spirit Airlines
27 Sep - 16 Oct Spirit Airlines
20 Sep - 05 Oct Spirit Airlines
27 Sep - 05 Oct Spirit Airlines
28 Sep - 16 Oct Spirit Airlines
06 Sep - 11 Sep Spirit Airlines
06 Sep - 22 Sep Spirit Airlines
06 Sep - 21 Sep Spirit Airlines
06 Sep - 19 Sep Spirit Airlines
20 Sep - 06 Oct Spirit Airlines
27 Sep - 17 Oct Spirit Airlines
27 Sep - 06 Oct Spirit Airlines
27 Sep - 11 Oct Spirit Airlines
21 Sep - 05 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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