Cheap flights from San Juan Luis Munoz Marin Intl Airport to Chicago from $109

The month of May is, on average, the cheapest month to fly to Chicago from San Juan Luis Munoz Marin Intl Airport, 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 San Juan Luis Munoz Marin Intl Airport 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 $454. 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 San Juan Luis Munoz Marin Intl Airport to Chicago for around $629.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from San Juan Luis Munoz Marin Intl Airport to Chicago during this time can be as low as $455. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $521.

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

You are more likely to see cheaper flights to Chicago from San Juan Luis Munoz Marin Intl Airport 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 San Juan Luis Munoz Marin Intl Airport for as low as $278 on momondo.

There are 4 cabin classes available to choose from on San Juan Luis Munoz Marin Intl Airport to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 11% on your flight if you consider stops on a San Juan Luis Munoz Marin Intl Airport to Chicago flight.

As of June 2026, prices for San Juan Luis Munoz Marin Intl Airport to Chicago flights are approximately 3% cheaper when compared to flights at the same time last year.

Southwest, Delta, and United Airlines are the most popular carriers operating from San Juan Luis Munoz Marin Intl to Chicago

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from San Juan Luis Munoz Marin Intl Airport 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 San Juan and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 183 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.

Atlanta (ATL) was the most common stop: 40% of momondo users choosing 1-stop flights on this route connected there.

Flights via New York (JFK) offer the lowest average round-trip price of $148.

Flights connecting via Atlanta (ATL) have the shortest average one-way travel time: 7h 03m.

Atlanta (ATL) has the shortest average layover time for this route: 1h 19m.

8 flights are operational daily from San Juan Luis Munoz Marin Intl Airport to Chicago as of June 2026. The most popular departure time for this route is 7:00AM, with 37% of flights per day taking off at noon.

The number of flights available between San Juan Luis Munoz Marin Intl Airport and Chicago is 56 per week as of June 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.