Cheapest return flights from Chicago to San Juan in October from 237€

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

Return flights

03 Oct - 06 Oct Frontier Airlines
06 Oct - 12 Oct Frontier Airlines
02 Oct - 06 Oct Frontier Airlines
02 Oct - 09 Oct Frontier Airlines
16 Oct - 20 Oct Frontier Airlines
31 Oct - 03 Nov Frontier Airlines
30 Oct - 03 Nov Frontier Airlines
09 Oct - 14 Oct Southwest Airlines
04 Oct - 07 Oct Southwest Airlines
21 Oct - 25 Oct Southwest Airlines
28 Oct - 01 Nov Southwest Airlines
01 Oct - 06 Oct Southwest Airlines
01 Oct - 04 Oct Southwest 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.

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