Cheap flights from Chicago to San Juan from $105

If you’re not able to fly to San Juan in May, then April is your next best option. Flight prices from Chicago to San Juan during April average around $328.

The cheapest day to depart from Chicago to San Juan is on a Tuesday when prices can be found for as low as $381. The most expensive day to fly to San Juan is Friday, with ticket prices averaging around $462.

The cheapest time of day to fly to San Juan is in the evening when flights can be purchased for as low as $378. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $485 on average. Flights to San Juan from Chicago at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago - San Juan flight prices

You are more likely to see cheaper flights to San Juan from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $386 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan from Chicago for as low as $346 on momondo.

Delta, Southwest, and United Airlines are the most popular carriers operating from Chicago to San Juan

Spirit Airlines, United Airlines and American Airlines are the top three most popular airlines that fly to San Juan from Chicago according to our data. Spirit Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to San Juan. Keep in mind that there are 7 different airlines that fly to San Juan on a routine basis, so you have a few additional options to choose from.

Historically, on average around 21% of flights between Chicago and San Juan have experienced a delay on any given week. The average delay length over the past 12 months has been 143 minutes.

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

Thursday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 19% of their flights experiencing any sort of delay.

8 flights are operational daily from Chicago to San Juan as of May 2026. The most popular departure time for this route is 8:00AM, with 63% of flights per day taking off at noon.

As of May 2026, there are 61 flights per week flying from Chicago to San Juan. The most common day of the week flights depart is Mon, with 15% of flights taking off on this day.