Cheapest return flights from Chicago to San Juan in August from 271€

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

Return flights

20 Aug - 02 Sep Delta
04 Aug - 11 Aug Frontier Airlines
11 Aug - 13 Aug Southwest Airlines
10 Aug - 13 Aug Southwest Airlines
20 Aug - 23 Aug Southwest Airlines
26 Aug - 30 Aug Southwest Airlines
09 Aug - 13 Aug Southwest Airlines
18 Aug - 19 Aug Southwest Airlines

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

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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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