Cheap flights from Chicago Midway Airport to Puerto Rico from $112

If you don’t want to visit Puerto Rico in February, then you should wait until April to fly from Chicago Midway Airport, when ticket prices are also cheap, with an average price of $264.

On average, the least expensive day to fly to Puerto Rico from Chicago Midway Airport is on a Sunday. momondo users have found tickets for Sunday departures for as low as $499. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Saturday, with ticket prices averaging around $572.

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

You are more likely to see cheaper flights to Puerto Rico from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $405 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 Midway Airport for as low as $326 on momondo.

Southwest is the most popular carrier operating from Chicago Midway to Puerto Rico

Southwest, Frontier and Delta are the top three most popular airlines that fly to Puerto Rico from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Puerto Rico. Keep in mind that there are 3 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 25% 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 123 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

Sunday 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, Southwest have had the least number of delays on this route over the last 12 months; with about 25% of their flights experiencing any sort of delay.