Cheapest one-way flights from Chicago to San Juan in June from $153

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

26 Jun Delta
06 Jun Frontier Airlines
05 Jun Frontier Airlines
09 Jun Frontier Airlines
08 Jun Frontier Airlines
23 Jun Allegiant Air
16 Jun Allegiant Air
24 Jun Southwest Airlines
25 Jun Southwest Airlines
08 Jun Southwest Airlines direct

Also check the deals for return flights from Chicago to San Juan in June.

Skyscanner

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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