Cheapest return flights from Chicago to San Juan in February from $138

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

Return flights

07 Feb - 09 Feb Frontier Airlines
06 Feb - 09 Feb Frontier Airlines
23 Feb - 27 Feb Frontier Airlines
02 Feb - 09 Feb Frontier Airlines
01 Feb - 09 Feb Frontier Airlines
20 Feb - 27 Feb Frontier Airlines
12 Feb - 19 Feb Frontier Airlines
07 Feb - 14 Feb Frontier Airlines
20 Feb - 22 Feb Frontier Airlines
19 Feb - 22 Feb Frontier Airlines
28 Feb - 06 Mar Frontier Airlines
28 Feb - 07 Mar Frontier Airlines
28 Feb - 04 Mar Southwest Airlines
27 Feb - 07 Mar Frontier Airlines
28 Feb - 03 Mar Southwest Airlines
27 Feb - 01 Mar Frontier Airlines
27 Feb - 02 Mar Frontier Airlines

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

Powered by

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.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.