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Cheap Flights from Chicago to San Juan $343.38

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Cheapest Flights from Chicago to San Juan (MDW to SJU)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to San Juan (MDW to SJU)

Question : How many days should you spend in San Juan?
Answer : Over the next two months, travelers from MDW to SJU are planning on staying for about one week on average.

Question : Have you considered flying out of an airport besides Chicago Midway International Airport (MDW)?
Answer : O'Hare International Airport is just 16 miles away, and, on average, flights are 37% cheaper for the next few months. Save a few bucks and put it toward your next trip.

Question : What's the likelihood of you being delayed on this route?
Answer : MDW to SJU currently scores 0 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 0 stars, you should feel rather worried about getting to San Juan on time.

Question : Can you cut down on flight costs by changing the day of the week you travel to San Juan?
Answer : For the month of April, the cheapest day to fly is Tuesday. Being flexible with your travel days garners even more savings during booking.

Question : Which airline is giving the best deals for round-trip flights from Chicago Midway International Airport (MDW) to Luis Munoz Marin International Airport (SJU)?
Answer : Delta Air Lines is offering the best deal at $307. Better take a look quickly because prices range all the way up to $1,028 over the next three months.

Question : Should you take that vacation to San Juan in the next 30 days?
Answer : Apr 4th has seen bookings (as of Mar 27th) as cheap as $307. That comes in 47% below the average price for this route. Saving on booking fees means you'll have more cash in your pocket for the trip.

Question : What price range should you expect when booking from Chicago (MDW) to San Juan (SJU)?
Answer : Flight prices are fluctuating more for this route than most routes from the United States, as they're ranging from $307 to $1,028. However, the sooner you book, the more you'll be able to save.