Cheapest return flights from Chicago to San Juan in February from $177

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

Return flights

21 Feb - 25 Feb Frontier Airlines
09 Feb - 14 Feb Frontier Airlines
05 Feb - 14 Feb Frontier Airlines
23 Feb - 28 Feb Frontier Airlines
27 Feb - 04 Mar Frontier Airlines
05 Feb - 08 Feb Frontier Airlines
01 Feb - 05 Feb Frontier Airlines
06 Feb - 14 Feb Frontier Airlines
08 Feb - 14 Feb Frontier Airlines
01 Feb - 04 Feb Frontier Airlines
24 Feb - 28 Feb Frontier Airlines
28 Feb - 06 Mar Frontier Airlines
24 Feb - 08 Mar Frontier Airlines
27 Feb - 08 Mar Frontier Airlines
27 Feb - 07 Mar Frontier Airlines
26 Feb - 01 Mar Frontier Airlines
01 Feb - 01 Mar Frontier Airlines
27 Feb - 14 Mar Frontier Airlines
26 Feb - 05 Mar Frontier Airlines
26 Feb - 03 Mar Southwest Airlines

Also check the deals for one-way flights from Chicago to San Juan in February.

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