Cheapest return flights from Chicago to San Juan in September from 407€

Best time to book flights for Chicago (MDW) to San Juan (SJU) flights at AirHint

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

Return flights

01 Sep - 05 Sep Southwest Airlines
12 Sep - 14 Sep Southwest Airlines
13 Sep - 15 Sep Delta
29 Sep - 03 Oct Delta

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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