$128 Find Cheap Flights from Chicago Midway Airport to San Juan - Compare and Save

Your flight ticket price will generally be cheaper if you fly to San Juan on a Sunday and more expensive on a Saturday. On your return trip to Chicago Midway Airport, you should consider flying back on a Saturday, and avoid Sundays for better deals.

The cheapest month for flights from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport is February, where tickets cost $243 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $556 and $544 respectively.

In the past 5 days, the cheapest round-trip tickets from Chicago Midway Airport to San Juan were found on Southwest ($256) and Frontier ($353).

There are 2 airlines that fly nonstop from Chicago Midway Airport to San Juan Luis Munoz Marin Intl Airport. They are Frontier and Southwest. The cheapest airline for this route is Frontier, with the best round-trip deal found costing $91. On average, the best prices for this route can be found at Frontier.

Weekly flights between Chicago and San Juan historically see delays in approximately 28% of cases, with the average delay over the past year being 127 minutes.

Typically, flights leaving in the early afternoon tend to face fewer delays, whereas flights in the morning have historically encountered delays more often.

Statistically, Wednesday 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, Southwest have experienced the fewest delays on this route in the past 12 months, with only about 27% of their flights encountering any delays.

Atlanta (ATL) is the top choice – 55% of KAYAK users who clicked on 1-stop flights from Chicago Midway Airport to San Juan picked an itinerary connecting there.

Flights via Tampa (TPA) offer the most affordable fares, with an average round-trip price of $453.

Consider flying via Baltimore (BWI) for the shortest journey. The average one-way travel time for flights connecting there is 6h 35m.

If you prefer a quick connection, Baltimore (BWI) often has the shortest layovers from Chicago Midway Airport to San Juan, with an average of 0h 46m.