Cheapest return flights from Chicago to San Juan in October from $270

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

Return flights

16 Oct - 25 Oct Frontier Airlines
24 Oct - 26 Oct Frontier Airlines
02 Oct - 17 Oct Frontier Airlines
16 Oct - 19 Oct Frontier Airlines
09 Oct - 12 Oct Frontier Airlines
03 Oct - 04 Oct Frontier Airlines
04 Oct - 06 Oct Frontier Airlines
03 Oct - 05 Oct Frontier Airlines
04 Oct - 04 Oct Frontier Airlines
31 Oct - 03 Nov Frontier Airlines
02 Oct - 06 Oct Frontier Airlines
25 Oct - 02 Nov Frontier Airlines
25 Oct - 19 Nov Frontier Airlines
25 Oct - 01 Nov Frontier Airlines
29 Oct - 01 Nov Southwest Airlines
25 Oct - 24 Nov 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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