Cheapest return flights from Chicago to San Jose in February from $391

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

Return flights

04 Feb - 08 Feb Frontier Airlines
11 Feb - 17 Feb Frontier Airlines
26 Feb - 01 Mar Frontier Airlines
12 Feb - 17 Feb Frontier Airlines
01 Feb - 05 Feb Delta
27 Feb - 06 Mar Frontier Airlines
19 Feb - 23 Feb Frontier Airlines
20 Feb - 23 Feb Frontier Airlines
12 Feb - 16 Feb Frontier Airlines
27 Feb - 02 Mar Frontier Airlines
23 Feb - 25 Feb Southwest Airlines
08 Feb - 13 Feb Southwest Airlines
26 Feb - 02 Mar Frontier Airlines
20 Feb - 22 Feb Frontier Airlines
28 Feb - 07 Mar Southwest Airlines
28 Feb - 06 Mar Southwest Airlines
27 Feb - 01 Mar Southwest Airlines

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

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