Cheapest return flights from Chicago to San Juan in January from 155€

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

Return flights

08 Jan - 14 Jan Frontier Airlines
07 Jan - 15 Jan Frontier Airlines
12 Jan - 15 Jan Frontier Airlines
09 Jan - 12 Jan Frontier Airlines
09 Jan - 14 Jan Frontier Airlines
11 Jan - 15 Jan Frontier Airlines
30 Jan - 02 Feb Frontier Airlines
22 Jan - 27 Jan Southwest Airlines
21 Jan - 27 Jan Southwest Airlines
28 Jan - 04 Feb Delta
10 Jan - 14 Jan Frontier Airlines
10 Jan - 15 Jan Frontier Airlines
29 Jan - 05 Feb Southwest Airlines
30 Jan - 03 Feb Frontier Airlines
28 Jan - 02 Feb Frontier Airlines
11 Jan - 11 Feb Southwest Airlines
30 Jan - 04 Feb Southwest Airlines
31 Jan - 07 Feb Southwest Airlines
31 Jan - 01 Feb Southwest Airlines

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

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