Cheapest return flights from Chicago to San Juan in August from $291

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

Return flights

19 Aug - 02 Sep Frontier Airlines
18 Aug - 25 Aug Frontier Airlines
10 Aug - 14 Aug Southwest Airlines
03 Aug - 14 Aug Southwest Airlines
03 Aug - 12 Aug Southwest Airlines
03 Aug - 10 Aug Frontier Airlines
22 Aug - 24 Aug Delta
20 Aug - 23 Aug Southwest Airlines
03 Aug - 15 Aug Southwest Airlines
03 Aug - 16 Aug Southwest Airlines
09 Aug - 10 Aug Southwest Airlines

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

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