Cheap flights from Puerto Rico to Chicago from $119

The month of May is, on average, the cheapest month to fly to Chicago from Puerto Rico, with most prices found around $64. If you’re not able to fly to Chicago in May, then October is your next best option. Flight prices from Puerto Rico to Chicago during October average around $83.

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $453. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Puerto Rico to Chicago for around $623.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Puerto Rico to Chicago during this time can be as low as $450. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $520.

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

You are more likely to see cheaper flights to Chicago from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $339 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Puerto Rico for as low as $278 on momondo.

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

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

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Puerto Rico according to our data. United Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

Historically, on average around 8% of flights between Puerto Rico and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 184 minutes.

Generally, flights departing at night 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. Saturday 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 4% of their flights experiencing any sort of delay.

The number of flights available between Puerto Rico and Chicago is 8 per day as of June 2026. The most frequent departure time is 7:00AM, with 37% of daily flights leaving at noon.

56 flights are operational weekly from Puerto Rico to Chicago as of June 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.