Cheapest one-way flights from Chicago to San Juan in July from 123€

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

One-Way flights

28 Jul Frontier Airlines
31 Jul Frontier Airlines
27 Jul Frontier Airlines
30 Jul Southwest Airlines
27 Jul Southwest Airlines direct

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

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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