Cheapest return flights from Chicago to San Juan in February from 155€

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

Return flights

19 Feb - 23 Feb Frontier Airlines
22 Feb - 26 Feb Frontier Airlines
02 Feb - 06 Feb Frontier Airlines
28 Feb - 06 Mar Frontier Airlines
16 Feb - 25 Feb Delta
05 Feb - 10 Feb Southwest Airlines
12 Feb - 01 Mar Frontier Airlines
26 Feb - 01 Mar Frontier Airlines
12 Feb - 15 Feb Frontier Airlines
05 Feb - 09 Feb Southwest Airlines
19 Feb - 22 Feb Frontier Airlines
14 Feb - 22 Feb Frontier Airlines
06 Feb - 09 Feb Frontier Airlines
20 Feb - 01 Mar Frontier Airlines
25 Feb - 02 Mar Southwest Airlines
25 Feb - 01 Mar Southwest Airlines

Also check the deals for one-way 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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