Cheapest one-way flights from Chicago to San Juan in June from $218
AirHint found the following cheapest one-way flights from Chicago (MDW) to San Juan (SJU) in June 2025 (see full year).
One-Way flights
Also check the deals for return 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.
