Cheapest one-way flights from Chicago to San Juan in February from 60€

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

One-Way flights

02 Feb Frontier Airlines
07 Feb Frontier Airlines
14 Feb Frontier Airlines
20 Feb Frontier Airlines
17 Feb Southwest Airlines
12 Feb Frontier Airlines
15 Feb Southwest Airlines
13 Feb Frontier Airlines
18 Feb Southwest Airlines
16 Feb Frontier Airlines

Also check the deals for return flights from Chicago to San Juan in February.

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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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