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

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

One-Way flights

18 Oct Spirit Airlines
15 Oct Frontier Airlines
25 Oct Frontier Airlines
02 Oct Spirit Airlines direct
16 Oct Spirit Airlines direct
31 Oct Spirit Airlines direct
23 Oct Spirit Airlines direct
06 Oct Spirit Airlines direct
17 Oct Spirit Airlines direct
12 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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