Cheapest one-way flights from Chicago to San Juan in October from $101

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

One-Way flights

16 Oct Frontier Airlines
02 Oct Spirit Airlines direct
05 Oct Spirit Airlines direct
16 Oct American Airlines direct
17 Oct Spirit Airlines direct
26 Oct Spirit Airlines direct
30 Oct Spirit Airlines direct
14 Oct Spirit Airlines
28 Oct Spirit Airlines
11 Oct Spirit Airlines direct

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

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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