Cheapest one-way flights from Chicago to San Juan in September from $92

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

One-Way flights

13 Sep Frontier Airlines
04 Sep Frontier Airlines
11 Sep Frontier Airlines
12 Sep Frontier Airlines
28 Sep Frontier Airlines
21 Sep Spirit Airlines
25 Sep Spirit Airlines
18 Sep Spirit Airlines
19 Sep Spirit Airlines direct
14 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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