Cheapest return flights from Chicago to San Juan in January from 132€

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

Return flights

07 Jan - 15 Jan Frontier Airlines
07 Jan - 14 Jan Frontier Airlines
09 Jan - 12 Jan Frontier Airlines
07 Jan - 12 Jan Frontier Airlines
31 Jan - 07 Feb Frontier Airlines
22 Jan - 29 Jan Frontier Airlines
07 Jan - 10 Jan Frontier Airlines
08 Jan - 15 Jan Frontier Airlines
23 Jan - 27 Jan Southwest Airlines
03 Jan - 10 Jan Frontier Airlines
05 Jan - 08 Jan Frontier Airlines
31 Jan - 01 Feb Southwest Airlines
31 Jan - 08 Feb Southwest Airlines
30 Jan - 01 Feb Frontier Airlines

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

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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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