Cheapest return flights from Chicago (MDW) to San Juan (SJU), September

Select a price to book. see full year.

Dates, airline, and price
Dates Airline Price
08 Sep 30 Sep Southwest Airlines
13 Sep 17 Sep Southwest Airlines
01 Sep 02 Sep Southwest Airlines
09 Sep 20 Sep Southwest Airlines
08 Sep 12 Sep Southwest Airlines
01 Sep 05 Sep Southwest Airlines
01 Sep 15 Sep Southwest Airlines
01 Sep 03 Sep Southwest Airlines
10 Sep 17 Sep Southwest Airlines
11 Sep 16 Sep Southwest Airlines
30 Sep 04 Oct Southwest Airlines
25 Sep 02 Oct Frontier Airlines
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deals for one-way flights from Chicago to San Juan in September.

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Updated Aug 25, 2026.

About these fares

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