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

27 Oct - 01 Nov Frontier Airlines
28 Oct - 01 Nov Frontier Airlines
30 Oct - 04 Nov Frontier Airlines
15 Oct - 20 Oct Frontier Airlines
10 Oct - 13 Oct Frontier Airlines
14 Oct - 21 Oct United direct
01 Oct - 07 Oct United
01 Oct - 04 Oct Frontier Airlines

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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