Cheapest return flights from Chicago to San Juan in October from 156€

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

Return flights

21 Oct - 28 Oct Frontier Airlines
28 Oct - 03 Nov Frontier Airlines
30 Oct - 06 Nov Frontier Airlines
31 Oct - 07 Nov Frontier Airlines
27 Oct - 31 Oct Frontier Airlines
31 Oct - 04 Nov Frontier Airlines
23 Oct - 27 Oct Frontier Airlines
23 Oct - 31 Oct Frontier Airlines
24 Oct - 31 Oct Frontier Airlines
20 Oct - 11 Nov Frontier Airlines
30 Oct - 01 Nov Frontier Airlines
20 Oct - 27 Oct Frontier Airlines
30 Oct - 03 Nov Frontier Airlines
20 Oct - 24 Oct Frontier Airlines
24 Oct - 27 Oct Frontier Airlines
23 Oct - 26 Oct Frontier Airlines
25 Oct - 01 Nov Frontier Airlines
19 Oct - 22 Oct Frontier Airlines
29 Oct - 03 Nov Southwest Airlines
29 Oct - 01 Nov Delta

Also check the deals for one-way flights from Chicago to San Juan in October.

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