Cheapest return flights from Chicago to San Juan in August from $410

Best time to book flights for Chicago (MDW) to San Juan (SJU) flights at AirHint

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

Return flights

12 Aug - 23 Aug Delta
12 Aug - 21 Aug Southwest Airlines
07 Aug - 14 Aug Frontier Airlines
14 Aug - 18 Aug Frontier Airlines
12 Aug - 20 Aug Southwest Airlines
12 Aug - 19 Aug Southwest Airlines
11 Aug - 19 Aug Southwest Airlines
21 Aug - 26 Aug Southwest Airlines
20 Aug - 25 Aug Southwest Airlines
04 Aug - 11 Aug 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.

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