[1][2] Los Chiles was originally settled by fishermen and others who worked on the nearby Río San Juan in Nicaragua.

During the 1980s, it was a strategic location on an important supply route for the Contras fighting to overthrow the Sandinista government in Nicaragua, and during that time military men from the United States were a common (albeit illegal) sight on the streets on the town.

[6] The district is covered by the following road routes: Los Chiles is served by Los Chiles Airport, a grass runway on the east side of town.

The Río Frío, on the western edge of town, is a major thoroughfare used to access small villages and farms in the surrounding area.

A gas station is located here, the only one for 20 kilometers in any direction, and a civil guard checkpoint is on Highway 35 south of town.