Cheapest one-way flights from Chicago to San Juan in August from 106€

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

One-Way flights

09 Aug Frontier Airlines
24 Aug Frontier Airlines
29 Aug Frontier Airlines
31 Aug Frontier Airlines
21 Aug Frontier Airlines
01 Aug Frontier Airlines
04 Aug Frontier Airlines
28 Aug Frontier Airlines
03 Aug Frontier Airlines
06 Aug Southwest Airlines

Also check the deals for return 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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