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

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

Return flights

14 Sep - 21 Sep Frontier Airlines
19 Sep - 22 Sep Frontier Airlines
04 Sep - 07 Sep Frontier Airlines
11 Sep - 14 Sep Frontier Airlines
11 Sep - 15 Sep Frontier Airlines
05 Sep - 08 Sep Frontier Airlines
04 Sep - 08 Sep Frontier Airlines
09 Sep - 23 Sep Southwest Airlines
10 Sep - 21 Sep Southwest Airlines
02 Sep - 07 Sep Southwest 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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