Cheap flights from Chicago to San Juan from $109

If you aren’t able to travel to San Juan Luis Munoz Marin Intl Airport during the month of August, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $341.

On average, the least expensive day to fly to San Juan Luis Munoz Marin Intl Airport from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $418. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $504.

The cheapest time of day to fly to San Juan Luis Munoz Marin Intl Airport is in the evening when flights can be purchased for as low as $358. Flights in the morning are often more expensive with an average ticket price of $523.

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

You are more likely to see cheaper flights to San Juan Luis Munoz Marin Intl Airport from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan Luis Munoz Marin Intl Airport for around $404 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan Luis Munoz Marin Intl Airport from Chicago for as low as $363 on momondo.

There are 4 cabin classes available to choose from on Chicago to San Juan Luis Munoz Marin Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 9% on your flight if you consider stops on a Chicago to San Juan Luis Munoz Marin Intl Airport flight.

As of September 2026, prices for Chicago to San Juan Luis Munoz Marin Intl Airport flights are approximately 27% more expensive when compared to flights at the same time last year.

United Airlines, American Airlines, and JetBlue are the most popular carriers operating from Chicago to San Juan Luis Munoz Marin Intl

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to San Juan Luis Munoz Marin Intl Airport from Chicago according to our data. United Airlines is the first choice among our users, with 42% of people opting to fly with this airline when traveling to San Juan Luis Munoz Marin Intl Airport. Keep in mind that there are 6 different airlines that fly to San Juan Luis Munoz Marin Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 23% 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 142 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.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Monday 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 18% of their flights experiencing any sort of delay.

New York (JFK) was the most common stop: 30% of momondo users choosing 1-stop flights on this route connected there.

Flights via Atlanta (ATL) offer the lowest average round-trip price of $246.

Flights connecting via Tampa (TPA) have the shortest average one-way travel time: 6h 55m.

Tampa (TPA) has the shortest average layover time for this route: 1h 10m.

The number of flights available between Chicago and San Juan Luis Munoz Marin Intl Airport is 3 per day as of September 2026. The most frequent departure time is 8:00AM, with 50% of daily flights leaving at noon.

21 flights are operational weekly from Chicago to San Juan Luis Munoz Marin Intl Airport as of September 2026. The most popular departure day for this route is Mon, with 19% of flights per week taking off on this day.