Cheapest return flights from Chicago to San Juan in August from $242

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

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

Return flights

04 Aug - 06 Aug Spirit Airlines direct
17 Aug - 23 Aug Spirit Airlines direct
18 Aug - 22 Aug Spirit Airlines direct
11 Aug - 15 Aug Spirit Airlines
12 Aug - 15 Aug Spirit Airlines
18 Aug - 26 Aug Spirit Airlines
04 Aug - 12 Aug Spirit Airlines direct
04 Aug - 10 Aug Spirit Airlines direct
09 Aug - 12 Aug Spirit Airlines direct
11 Aug - 15 Aug Spirit Airlines direct

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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