Cheapest one-way flights from Chicago to San Juan in January from 96€

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

One-Way flights

26 Jan Frontier Airlines
28 Jan Southwest Airlines
20 Jan Delta
21 Jan Delta
23 Jan Frontier Airlines
17 Jan Frontier Airlines
29 Jan Southwest Airlines
15 Jan Frontier Airlines
17 Jan Southwest Airlines direct

Also check the deals for return 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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