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

Select a price to book. see full year.

Dates, airline, and price
Dates Airline Price
22 Oct 26 Oct Southwest Airlines
22 Oct 27 Oct Southwest Airlines
14 Oct 21 Oct Frontier Airlines
06 Oct 13 Oct Frontier Airlines
13 Oct 16 Oct Frontier Airlines
08 Oct 13 Oct Frontier Airlines
02 Oct 08 Oct Southwest Airlines
22 Oct 22 Oct Southwest Airlines
02 Oct 05 Oct Southwest Airlines
16 Oct 23 Oct Southwest Airlines
31 Oct 03 Nov Frontier Airlines
23 Oct 01 Nov Southwest Airlines
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deals for one-way flights from Chicago to San Juan in October.

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Updated Jul 8, 2026.

About these fares

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