AirHint found the following cheapest one-way flights from Chicago (MDW) to San Juan (SJU) in July 2025 (see full year).
One-Way flights
| 31 Jul | Frontier Airlines | ||
| 24 Jul | Frontier Airlines | ||
| 18 Jul | Frontier Airlines | ||
| 28 Jul | Frontier Airlines | ||
| 20 Jul | Southwest Airlines | direct | |
| 09 Jul | Delta | ||
| 06 Jul | Southwest Airlines | direct |
Also check the deals for return flights from Chicago to San Juan in July.
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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