Cheapest return flights from Chicago to San Juan in August from $184

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

Return flights

23 Aug - 30 Aug Frontier Airlines
23 Aug - 28 Aug Frontier Airlines
24 Aug - 30 Aug Frontier Airlines
16 Aug - 20 Aug Frontier Airlines
13 Aug - 20 Aug Frontier Airlines
21 Aug - 28 Aug Frontier Airlines
22 Aug - 29 Aug Frontier Airlines
31 Aug - 04 Sep Frontier Airlines
16 Aug - 21 Aug Frontier Airlines
16 Aug - 24 Aug Frontier Airlines
30 Aug - 03 Sep Frontier Airlines
28 Aug - 31 Aug Frontier Airlines
28 Aug - 01 Sep Frontier Airlines
30 Aug - 18 Sep Spirit Airlines direct
30 Aug - 19 Sep Spirit Airlines direct
18 Aug - 05 Sep Spirit Airlines
21 Aug - 05 Sep Spirit Airlines
24 Aug - 05 Sep Spirit Airlines
31 Aug - 18 Sep Spirit Airlines direct
31 Aug - 19 Sep 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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