Cheap flights from Chicago to Puerto Rico from $97

If you don’t want to visit Puerto Rico in August, then you should wait until January to fly from Chicago, when ticket prices are also cheap, with an average price of $346.

On average, the least expensive day to fly to Puerto Rico from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $422. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Thursday, with ticket prices averaging around $509.

Our most recent data shows that the best time of day to fly to Puerto Rico is in the evening. Flights from Chicago to Puerto Rico during this time can be as low as $361. In contrast, the most expensive time of day to depart to Puerto Rico is in the morning when prices are around $523.

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

You are more likely to see cheaper flights to Puerto Rico from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $403 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Chicago for as low as $355 on momondo.

There are 4 cabin classes available to choose from on Chicago to Puerto Rico flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest, United Airlines, and JetBlue are the most popular carriers operating from Chicago to Puerto Rico

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Puerto Rico from Chicago according to our data. United Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Puerto Rico. Keep in mind that there are 6 different airlines that fly to Puerto Rico on a routine basis, so you have a few additional options to choose from.

Historically, on average around 23% of flights between Chicago and Puerto Rico have experienced a delay on any given week. The average delay length over the past 12 months has been 138 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. 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 18% of their flights experiencing any sort of delay.

6 flights are operational daily from Chicago to Puerto Rico as of August 2026. The most popular departure time for this route is 8:00AM, with 51% of flights per day taking off in the afternoon.

As of August 2026, there are 44 flights per week flying from Chicago to Puerto Rico. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.