Cheap flights from Puerto Rico to Chicago from $108

The month of January is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Puerto Rico averaging around $255.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $427. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Puerto Rico because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $615.

Flying to Chicago O'Hare Intl Airport from Puerto Rico at noon is the least expensive time of day to depart. momondo users have found prices as low as $422 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $516. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Puerto Rico when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $343 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Puerto Rico for as low as $214 on momondo.

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

United Airlines, JetBlue, and American Airlines are the most popular carriers operating from Puerto Rico to Chicago O'Hare Intl

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Puerto Rico according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 5 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 9% 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 187 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. 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 4% of their flights experiencing any sort of delay.

3 flights are operational daily from Puerto Rico to Chicago O'Hare Intl Airport as of September 2026. The most popular departure time for this route is 3:00PM, with 100% of flights per day taking off in the afternoon.

As of September 2026, 21 flights take off from Puerto Rico and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 14% of weekly flights taking off on this day.