Cheap flights from Illinois to Puerto Rico from $90

If you don’t want to visit Puerto Rico in August, then you should wait until January to fly from Illinois, when ticket prices are also cheap, with an average price of $343.

On average, the least expensive day to fly to Puerto Rico from Illinois 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. The most expensive day to fly to Puerto Rico is Thursday, with ticket prices averaging around $504.

Our most recent data shows that the best time of day to fly to Puerto Rico is in the evening. Flights from Illinois to Puerto Rico during this time can be as low as $358. 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 Illinois - Puerto Rico flight prices

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

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

Frontier, United Airlines, and JetBlue are the most popular carriers operating from Illinois to Puerto Rico

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Puerto Rico from Illinois 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 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.

As of September 2026, there are 3 flights per day flying from Illinois to Puerto Rico. The most common time of day flights depart is 8:00AM, with 50% of flights taking off at noon.

As of September 2026, 21 flights take off from Illinois and land in Puerto Rico each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.