Cheapest return flights from Chicago to San Juan in August from $213

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

Return flights

31 Aug - 20 Sep Spirit Airlines
25 Aug - 13 Sep Spirit Airlines
25 Aug - 29 Aug Spirit Airlines
25 Aug - 27 Aug Spirit Airlines
25 Aug - 11 Sep Spirit Airlines
25 Aug - 04 Sep Spirit Airlines
31 Aug - 13 Sep Spirit Airlines
25 Aug - 12 Sep Spirit Airlines
25 Aug - 06 Sep Spirit Airlines
22 Aug - 29 Aug Spirit Airlines
31 Aug - 11 Sep Spirit Airlines
31 Aug - 18 Sep Spirit Airlines
31 Aug - 19 Sep Spirit Airlines
22 Aug - 23 Aug Spirit Airlines
22 Aug - 27 Aug Spirit Airlines
22 Aug - 28 Aug Spirit Airlines
25 Aug - 30 Aug Spirit Airlines
26 Aug - 29 Aug Spirit Airlines
26 Aug - 27 Aug Spirit Airlines
26 Aug - 28 Aug Spirit 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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