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
27 Oct 31 Oct Southwest Airlines
19 Oct 26 Oct Southwest Airlines
09 Oct 12 Oct Southwest Airlines
09 Oct 16 Oct Southwest Airlines
17 Oct 21 Oct Frontier Airlines
07 Oct 14 Oct Southwest Airlines
15 Oct 19 Oct Southwest Airlines
30 Oct 02 Nov Southwest Airlines
29 Oct 02 Nov Southwest Airlines
16 Oct 20 Oct Frontier Airlines
04 Oct 21 Oct Frontier Airlines
31 Oct 03 Nov Frontier Airlines
08 Oct 11 Oct Southwest Airlines
29 Oct 01 Nov Southwest Airlines
23 Oct 01 Nov Southwest Airlines
21 Oct 01 Nov Frontier Airlines
25 Oct 03 Nov Frontier Airlines
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deals for one-way flights from Chicago to San Juan in October.

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Updated Aug 25, 2026.

About these fares

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