Cheapest return flights from Chicago to San Juan in June from $344

Best time to book flights for Chicago (MDW) to San Juan (SJU) flights at AirHint

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

Return flights

07 Jun - 11 Jun Frontier Airlines
06 Jun - 10 Jun Frontier Airlines
09 Jun - 16 Jun Frontier Airlines
04 Jun - 09 Jun Frontier Airlines
02 Jun - 09 Jun Frontier Airlines
01 Jun - 05 Jun Frontier Airlines
06 Jun - 11 Jun Frontier Airlines
04 Jun - 12 Jun Frontier Airlines
10 Jun - 16 Jun Frontier Airlines
10 Jun - 18 Jun Southwest Airlines
30 Jun - 07 Jul Southwest Airlines
27 Jun - 01 Jul Southwest Airlines
27 Jun - 04 Jul Frontier Airlines
27 Jun - 05 Jul Frontier Airlines
30 Jun - 08 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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