Cheapest return flights from Chicago to San Juan in January from 226€

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

Return flights

21 Jan - 30 Jan Southwest Airlines
20 Jan - 27 Jan Southwest Airlines
25 Jan - 31 Jan Southwest Airlines
21 Jan - 28 Jan Southwest Airlines
21 Jan - 29 Jan Southwest Airlines
25 Jan - 03 Feb Southwest Airlines
13 Jan - 17 Jan Southwest Airlines
12 Jan - 26 Jan Southwest Airlines
20 Jan - 24 Feb Southwest Airlines
07 Jan - 13 Jan Frontier Airlines
13 Jan - 18 Jan Southwest Airlines
07 Jan - 11 Jan Frontier Airlines
30 Jan - 01 Feb Southwest Airlines
29 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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