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

04 Sep - 07 Sep Frontier Airlines
05 Sep - 07 Sep Frontier Airlines
15 Sep - 18 Sep Frontier Airlines
19 Sep - 22 Sep Frontier Airlines
12 Sep - 14 Sep Frontier Airlines
18 Sep - 22 Sep Frontier Airlines
11 Sep - 14 Sep Frontier Airlines
12 Sep - 18 Sep Frontier Airlines
11 Sep - 18 Sep Frontier Airlines
22 Sep - 29 Sep Frontier Airlines
05 Sep - 10 Oct Frontier Airlines
28 Sep - 16 Oct Spirit Airlines
22 Sep - 07 Oct Spirit Airlines
28 Sep - 16 Oct Spirit Airlines direct
18 Sep - 07 Oct Spirit Airlines
28 Sep - 07 Oct Spirit Airlines
21 Sep - 07 Oct Spirit Airlines
25 Sep - 07 Oct Spirit Airlines
19 Sep - 07 Oct Spirit Airlines
22 Sep - 11 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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