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

Select a price to book. see full year.

Dates, airline, and price
Dates Airline Price
06 Jan 13 Jan Southwest Airlines
28 Jan 01 Feb Southwest Airlines
03 Jan 12 Jan Southwest Airlines
15 Jan 22 Jan Southwest Airlines
02 Jan 06 Jan Southwest Airlines
01 Jan 09 Jan Southwest Airlines
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deals for one-way flights from Chicago to San Juan in January.

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Updated Jul 8, 2026.

About these fares

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