Cheapest return flights from Chicago to San Juan in August from $245

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

Return flights

09 Aug - 25 Aug Frontier Airlines
21 Aug - 24 Aug Frontier Airlines
21 Aug - 25 Aug Frontier Airlines
29 Aug - 01 Sep Frontier Airlines
28 Aug - 01 Sep Frontier Airlines
14 Aug - 18 Aug Frontier Airlines
16 Aug - 18 Aug Frontier Airlines
08 Aug - 11 Aug Frontier Airlines
07 Aug - 11 Aug Frontier Airlines
07 Aug - 10 Aug Frontier Airlines
22 Aug - 29 Aug Frontier Airlines
21 Aug - 27 Aug Frontier Airlines
28 Aug - 02 Sep Southwest Airlines
29 Aug - 02 Sep Southwest Airlines

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

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.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.