Cheapest one-way flights from Chicago to San Juan in September from 101€

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

One-Way flights

20 Sep Frontier Airlines
27 Sep Frontier Airlines
06 Sep Frontier Airlines
13 Sep Frontier Airlines
07 Sep Spirit Airlines
21 Sep Spirit Airlines
28 Sep Spirit Airlines
15 Sep Spirit Airlines direct
08 Sep Spirit Airlines direct
18 Sep Spirit Airlines direct

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

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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