Cheapest one-way flights from Chicago to San Juan in June from $119

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

One-Way flights

13 Jun Frontier Airlines
26 Jun Frontier Airlines
20 Jun Frontier Airlines
21 Jun Frontier Airlines
14 Jun Frontier Airlines
19 Jun Frontier Airlines
27 Jun Frontier Airlines
30 Jun Frontier Airlines
23 Jun Frontier Airlines
29 Jun Frontier Airlines

Also check the deals for return 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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