Cheapest return flights from Chicago to San Juan in August from $232

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

13 Aug - 23 Aug Spirit Airlines direct
12 Aug - 15 Aug Spirit Airlines
12 Aug - 21 Aug Spirit Airlines
08 Aug - 11 Aug Spirit Airlines
10 Aug - 14 Aug Spirit Airlines
10 Aug - 15 Aug Spirit Airlines
16 Aug - 20 Aug Spirit Airlines
21 Aug - 26 Aug Spirit Airlines direct
12 Aug - 19 Aug Spirit Airlines
26 Aug - 01 Sep Spirit Airlines
24 Aug - 31 Aug Spirit Airlines
28 Aug - 03 Sep Frontier Airlines
28 Aug - 01 Sep Frontier Airlines
26 Aug - 02 Sep Spirit Airlines direct
27 Aug - 01 Sep Spirit Airlines
27 Aug - 02 Sep Spirit Airlines
28 Aug - 03 Sep Spirit Airlines direct
28 Aug - 02 Sep Spirit Airlines direct
27 Aug - 02 Sep United direct
26 Aug - 01 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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