Cheapest one-way flights from Chicago to San Juan in August from 121€

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

One-Way flights

25 Aug Frontier Airlines
15 Aug Frontier Airlines
17 Aug Frontier Airlines
16 Aug Frontier Airlines
18 Aug Frontier Airlines
22 Aug Frontier Airlines
21 Aug Frontier Airlines
07 Aug Frontier Airlines
12 Aug Southwest Airlines
13 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.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.