Cheapest one-way flights from Chicago to San Juan in June from $218

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

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

One-Way flights

10 Jun Southwest Airlines
25 Jun Southwest Airlines
09 Jun Frontier Airlines
23 Jun Frontier Airlines
26 Jun Frontier Airlines
08 Jun Frontier Airlines
07 Jun Frontier Airlines
27 Jun Frontier Airlines
19 Jun Frontier Airlines
11 Jun Southwest 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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