Cheapest return flights from Chicago to San Juan in September from 137€

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

Return flights

22 Sep - 11 Oct Spirit Airlines
26 Sep - 11 Oct Spirit Airlines
25 Sep - 11 Oct Spirit Airlines
29 Sep - 11 Oct Spirit Airlines direct
26 Sep - 11 Oct Spirit Airlines direct
27 Sep - 11 Oct Spirit Airlines
28 Sep - 11 Oct Spirit Airlines direct
22 Sep - 11 Oct Spirit Airlines direct
21 Sep - 11 Oct Spirit Airlines direct
22 Sep - 07 Oct Spirit Airlines
22 Sep - 27 Sep Spirit Airlines
26 Sep - 27 Sep Spirit Airlines
25 Sep - 27 Sep Spirit Airlines
22 Sep - 25 Sep Spirit Airlines
22 Sep - 30 Sep Spirit Airlines
22 Sep - 26 Sep Spirit Airlines
26 Sep - 30 Sep Spirit Airlines
21 Sep - 27 Sep Spirit Airlines
25 Sep - 30 Sep Spirit Airlines
27 Sep - 30 Sep Spirit Airlines

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

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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