Cheapest return flights from Chicago to San Juan in October from 214€

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

Return flights

12 Oct - 18 Oct Frontier Airlines
03 Oct - 16 Oct Spirit Airlines direct
03 Oct - 05 Oct Spirit Airlines direct
03 Oct - 19 Oct Spirit Airlines direct
03 Oct - 11 Oct Spirit Airlines direct
03 Oct - 18 Oct Spirit Airlines direct
17 Oct - 19 Oct Spirit Airlines direct
17 Oct - 25 Oct Spirit Airlines direct
17 Oct - 26 Oct Spirit Airlines direct
17 Oct - 18 Oct Spirit Airlines direct
31 Oct - 03 Nov Frontier Airlines
17 Oct - 06 Nov Spirit Airlines direct
19 Oct - 07 Nov Spirit Airlines direct
19 Oct - 06 Nov Spirit Airlines direct
25 Oct - 07 Nov Spirit Airlines direct
25 Oct - 06 Nov Spirit Airlines direct
25 Oct - 09 Nov Spirit Airlines direct
17 Oct - 04 Nov Spirit Airlines
19 Oct - 04 Nov Spirit Airlines
16 Oct - 04 Nov Spirit Airlines

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.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.