Cheapest one-way flights from Chicago to San Juan in February from $105

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

One-Way flights

28 Feb Spirit Airlines
04 Feb Spirit Airlines direct
05 Feb Spirit Airlines direct
03 Feb Spirit Airlines direct
07 Feb Spirit Airlines direct
09 Feb Spirit Airlines direct
10 Feb Spirit Airlines direct
27 Feb Spirit Airlines
20 Feb Spirit Airlines direct
28 Feb Spirit Airlines direct

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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