$123 Find Cheap Flights from San Juan to Chicago - Compare and Save

The cheapest return flight from San Juan Luis Munoz Marin Intl Airport to Chicago costs $208 on the route between San Juan Luis Munoz Marin Intl Airport (SJU) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 45% cheaper than other San Juan Luis Munoz Marin Intl Airport-Chicago routes. It is also the most popular route.

If you are looking for a flight deal from San Juan to Chicago, look for departures on Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Tuesday is the cheapest day to fly and Thursday is the most expensive.

The cheapest month for flights from San Juan Luis Munoz Marin Intl Airport to Chicago is February, where tickets cost $220 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $447 and $381 respectively.

No, with an average price for the route of $356, prices are generally cheapest when you fly direct.

In the past 5 days, the cheapest round-trip tickets from San Juan to Chicago were found on Frontier ($188) and American Airlines ($247).

American Airlines connects San Juan to Chicago with 7 flights per week and both Frontier and United Airlines also offer 7 flights per week.

Weekly flights between San Juan and Chicago historically see delays in approximately 9% of cases, with the average delay over the past year being 184 minutes.

Typically, flights leaving at night tend to face fewer delays, whereas flights in the evening have historically encountered delays more often.

Statistically, Thursday is the day of the week with the fewest delays on this flight route, while Saturday has typically experienced more delays than other days.

Based on our data, United Airlines have experienced the fewest delays on this route in the past 12 months, with only about 4% of their flights encountering any delays.

New York (JFK) is the top choice – 35% of KAYAK users who clicked on 1-stop flights from San Juan to Chicago picked an itinerary connecting there.

Flights via Boston (BOS) offer the most affordable fares, with an average round-trip price of $157.

Consider flying via Atlanta (ATL) for the shortest journey. The average one-way travel time for flights connecting there is 7h 04m.

If you prefer a quick connection, Philadelphia (PHL) often has the shortest layovers from San Juan to Chicago, with an average of 0h 47m.

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Each day, there are 3 nonstop flights that take off from San Juan Luis Munoz Marin Intl Airport and land in Chicago, with an average flight time of 5h 09m. The most common departure time is 12:00 am and most flights take off in the evening. Each week, there are 21 flights and there are the same amount of flights each day (3).