Cheap flights from Chicago Midway Airport to San Juan from $129

If you’re not able to fly to San Juan in February, then October is your next best option. Flight prices from Chicago Midway Airport to San Juan during October average around $259.

The cheapest day to depart from Chicago Midway Airport to San Juan is on a Tuesday when prices can be found for as low as $419. The most expensive day to fly to San Juan is Thursday, with ticket prices averaging around $506.

The cheapest time of day to fly to San Juan is in the evening when flights can be purchased for as low as $371. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $523 on average. Flights to San Juan from Chicago Midway Airport in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

You are more likely to see cheaper flights to San Juan from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Juan for around $408 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Juan from Chicago Midway Airport for as low as $283 on momondo.

There is only 1 cabin class available to choose from on Chicago Midway Airport to San Juan flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Southwest is the most popular carrier operating from Chicago Midway to San Juan

Southwest, Frontier and Delta are the top three most popular airlines that fly to San Juan from Chicago Midway Airport according to our data. Southwest is the first choice among our users, with 61% of people opting to fly with this airline when traveling to San Juan. Keep in mind that there are 3 different airlines that fly to San Juan on a routine basis, so you have a few additional options to choose from.

Historically, on average around 25% of flights between Chicago and San Juan 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.