Cheapest return flights from Chicago to San Juan in August from 427€

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

30 Aug - 03 Sep Southwest Airlines
19 Aug - 23 Aug Southwest Airlines
30 Aug - 06 Sep Southwest Airlines
08 Aug - 15 Aug Southwest Airlines
01 Aug - 05 Aug Southwest Airlines
03 Aug - 07 Aug Southwest Airlines
01 Aug - 04 Aug Southwest Airlines
08 Aug - 13 Aug Frontier Airlines
02 Aug - 09 Aug Frontier Airlines
01 Aug - 08 Aug Frontier 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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