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

Return flights

03 Jun - 09 Jun	Delta
12 Jun - 17 Jun	Delta
01 Jun - 08 Jun	Delta
09 Jun - 16 Jun	Delta
18 Jun - 21 Jun	Delta
17 Jun - 21 Jun	Delta
04 Jun - 07 Jun	Delta
11 Jun - 14 Jun	Delta
10 Jun - 15 Jun	Delta
11 Jun - 16 Jun	Delta

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

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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Cheapest return flights from Chicago to San Juan in June from $645

Return flights