Cheapest return flights from Chicago to San Juan in January from $284

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

Return flights

08 Jan - 11 Jan Frontier Airlines
30 Jan - 02 Feb Frontier Airlines
17 Jan - 24 Jan Frontier Airlines
09 Jan - 20 Jan Delta
02 Jan - 20 Jan Delta
28 Jan - 01 Feb Southwest Airlines
03 Jan - 13 Jan Southwest Airlines
02 Jan - 07 Jan Frontier Airlines
03 Jan - 11 Jan Frontier Airlines
02 Jan - 05 Jan Frontier Airlines

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

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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