Cheapest return flights from Chicago to San Juan in August from $238

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

02 Aug - 16 Aug Frontier Airlines
02 Aug - 09 Aug Frontier Airlines
03 Aug - 08 Aug Spirit Airlines direct
16 Aug - 24 Aug Frontier Airlines
20 Aug - 23 Aug Spirit Airlines direct
09 Aug - 13 Aug Spirit Airlines direct
17 Aug - 27 Aug Spirit Airlines direct
23 Aug - 27 Aug Spirit Airlines direct
16 Aug - 23 Aug Spirit Airlines direct
16 Aug - 21 Aug Frontier Airlines
29 Aug - 04 Sep Frontier Airlines
29 Aug - 05 Sep Frontier Airlines
28 Aug - 03 Sep Frontier Airlines
26 Aug - 03 Sep Spirit Airlines direct
28 Aug - 01 Sep Frontier Airlines
27 Aug - 01 Sep Spirit Airlines
27 Aug - 03 Sep Spirit Airlines direct
29 Aug - 02 Sep Frontier Airlines
28 Aug - 02 Sep Frontier Airlines
29 Aug - 04 Sep United 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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