Cheap flights from Chicago to Santiago from $355

In general, June is the cheapest month to fly from Chicago to Santiago. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $666. If you don’t want to visit Santiago in June, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $714.

You are more likely to see cheaper flights to Santiago from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Santiago for around $926 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Santiago from Chicago for as low as $701 on momondo.

You could potentially save up to 22% on your flight if you consider stops on a Chicago to Santiago flight.

As of November 2026, prices for Chicago to Santiago flights are approximately 45% more expensive when compared to flights at the same time last year.

Arajet, Air Canada, and LATAM Airlines are the most popular carriers operating from Chicago to Santiago Arturo Merino Benitez

American Airlines, Copa Airlines and LATAM Airlines are the top three most popular airlines that fly to Santiago from Chicago according to our data. American Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Santiago. Keep in mind that there are 6 different airlines that fly to Santiago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 0% of flights between Chicago and Santiago have experienced a delay on any given week. The average delay length over the past 12 months has been 0 minutes.

Generally, flights departing in the early afternoon tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Bogotá (BOG) was the most common stop: 36% of momondo users choosing 1-stop flights on this route connected there.

Flights via New York (JFK) offer the lowest average round-trip price of $635.

Flights connecting via Houston (IAH) have the shortest average one-way travel time: 12h 53m.

Houston (IAH) has the shortest average layover time for this route: 1h 23m.