Cheapest return flights from Chicago to San Juan in October from 216€

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

Return flights

18 Oct - 30 Oct Spirit Airlines
18 Oct - 26 Oct Spirit Airlines
18 Oct - 22 Oct Spirit Airlines
18 Oct - 25 Oct Spirit Airlines
18 Oct - 21 Oct Spirit Airlines
18 Oct - 28 Oct Spirit Airlines
18 Oct - 27 Oct Spirit Airlines
18 Oct - 29 Oct Spirit Airlines
18 Oct - 24 Oct Spirit Airlines
18 Oct - 20 Oct Spirit Airlines
18 Oct - 03 Nov Spirit Airlines
18 Oct - 06 Nov Spirit Airlines
16 Oct - 03 Nov Spirit Airlines direct
16 Oct - 06 Nov Spirit Airlines direct
31 Oct - 14 Nov Spirit Airlines direct
31 Oct - 17 Nov Spirit Airlines direct
31 Oct - 20 Nov Spirit Airlines direct
31 Oct - 09 Nov Spirit Airlines direct
31 Oct - 03 Nov Spirit Airlines direct
31 Oct - 06 Nov Spirit Airlines direct

Also check the deals for one-way 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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