Cheapest return ORD–SJU flights, October

AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in October 2026 (see full year).

Return flights

07 Oct - 15 Oct Spirit Airlines direct
07 Oct - 21 Oct Spirit Airlines direct
07 Oct - 14 Oct Spirit Airlines direct
07 Oct - 20 Oct Spirit Airlines direct
07 Oct - 08 Oct Spirit Airlines
03 Oct - 06 Oct Spirit Airlines direct
24 Oct - 14 Nov Spirit Airlines direct
05 Oct - 06 Oct Spirit Airlines direct
05 Oct - 20 Oct Spirit Airlines direct
14 Oct - 21 Oct Spirit Airlines direct
19 Oct - 20 Oct Spirit Airlines direct
24 Oct - 11 Nov Spirit Airlines direct
25 Oct - 14 Nov Spirit Airlines direct
25 Oct - 11 Nov Spirit Airlines direct

Also check the deals for one-way flights from Chicago to San Juan in October.

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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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