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

One-Way flights

10 Aug	Frontier Airlines
18 Aug	Frontier Airlines
11 Aug	Frontier Airlines
25 Aug	Spirit Airlines
12 Aug	Frontier Airlines
24 Aug	Spirit Airlines
25 Aug	Spirit Airlines	direct
01 Aug	Frontier Airlines
09 Aug	Spirit Airlines	direct
16 Aug	Spirit Airlines	direct

Also check the deals for return flights from Chicago to San Juan in August.

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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Cheapest one-way flights from Chicago to San Juan in August from 83€

One-Way flights