Cheapest return flights from Chicago to San Juan in June from $211

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in June 2025 (see full year).

Return flights

14 Jun - 18 Jun Frontier Airlines
12 Jun - 19 Jun Frontier Airlines
23 Jun - 27 Jun Frontier Airlines
23 Jun - 26 Jun Frontier Airlines
14 Jun - 21 Jun Frontier Airlines
16 Jun - 19 Jun Frontier Airlines
16 Jun - 20 Jun Frontier Airlines
21 Jun - 29 Jun Frontier Airlines
12 Jun - 16 Jun Frontier Airlines
28 Jun - 30 Jun Frontier Airlines
30 Jun - 03 Jul Frontier Airlines
27 Jun - 06 Jul Frontier Airlines
17 Jun - 17 Jul Southwest Airlines
26 Jun - 01 Jul Frontier Airlines
28 Jun - 01 Jul Frontier Airlines

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

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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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