Cheapest return flights from Chicago to San Juan in January from $179

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in January 2026 (see full year).

Return flights

12 Jan - 17 Jan Frontier Airlines
12 Jan - 15 Jan Frontier Airlines
12 Jan - 22 Jan Frontier Airlines
10 Jan - 13 Jan Frontier Airlines
15 Jan - 22 Jan Frontier Airlines
17 Jan - 22 Jan Frontier Airlines
08 Jan - 15 Jan Frontier Airlines
07 Jan - 12 Jan Frontier Airlines
07 Jan - 13 Jan Frontier Airlines
10 Jan - 17 Jan Frontier Airlines
30 Jan - 08 Feb Frontier Airlines
30 Jan - 03 Feb Frontier Airlines
28 Jan - 02 Feb Frontier Airlines
31 Jan - 06 Feb Southwest Airlines
28 Jan - 01 Feb Frontier Airlines

Also check the deals for one-way flights from Chicago to San Juan in January.

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