Cheapest one-way flights from Chicago to San Juan in January from $61

Best time to book flights for Chicago (MDW) to San Juan (SJU) flights at AirHint

AirHint found the following cheapest one-way flights from Chicago (MDW) to San Juan (SJU) in January 2025 (see full year).

One-Way flights

24 Jan Frontier Airlines
10 Jan Frontier Airlines
31 Jan Frontier Airlines
06 Jan Frontier Airlines
13 Jan Frontier Airlines
30 Jan Frontier Airlines
03 Jan Frontier Airlines
02 Jan Frontier Airlines
09 Jan Frontier Airlines
29 Jan Southwest Airlines

Also check the deals for return 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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