Cheapest return flights from Chicago to San Juan in October from $193

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

Return flights

03 Oct - 07 Oct Frontier Airlines
06 Oct - 11 Oct Frontier Airlines
03 Oct - 11 Oct Frontier Airlines
15 Oct - 22 Oct Frontier Airlines
09 Oct - 13 Oct Frontier Airlines
31 Oct - 03 Nov Frontier Airlines
23 Oct - 27 Oct Frontier Airlines
17 Oct - 19 Oct Frontier Airlines
08 Oct - 13 Oct Frontier Airlines
05 Oct - 19 Oct Frontier Airlines
18 Oct - 22 Oct Frontier Airlines
29 Oct - 01 Nov jetBlue
28 Oct - 05 Nov jetBlue
25 Oct - 03 Nov Spirit Airlines direct
25 Oct - 09 Nov Spirit Airlines direct
25 Oct - 12 Nov Spirit Airlines
28 Oct - 05 Nov United direct
31 Oct - 03 Nov United direct
31 Oct - 09 Nov Spirit Airlines direct
16 Oct - 03 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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