Question 1

What is the cheapest month to book a flight from Chicago to San Juan Isla Grande Airport?

Accepted Answer

Currently, September is the cheapest month in which you can book a flight from Chicago to San Juan Isla Grande Airport (average of $164). Flying from Chicago to San Juan Isla Grande Airport in June is currently the most expensive (average of $344). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Question 2

What is the cheapest day to fly from Chicago to San Juan Isla Grande Airport?

Accepted Answer

Travelers seeking maximum savings on their Chicago to San Juan Isla Grande Airport flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Question 3

E

Accepted Answer

In terms of precipitation, rainfall in San Juan Isla Grande Airport ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit San Juan Isla Grande Airport when rainfall is around 2.2 in.

Question 4

E

Accepted Answer

If weather is an important factor for your trip to San Juan Isla Grande Airport, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Question 5

What is the cheapest day to fly round-trip from Chicago to San Juan Isla Grande Airport?

Accepted Answer

It’s generally more expensive to depart on a Wednesday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

Question 6

How far in advance should I book a flight from Chicago to San Juan Isla Grande Airport?

Accepted Answer

To save up to 31% on this flight, we recommend booking at least 43 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Chicago to San Juan Isla Grande Airport from $289 1-2 weeks out and tickets from $325 for flights departing within the next 72 hours.

Question 7

What is the cheapest month to fly from Chicago to San Juan Isla Grande Airport?

Accepted Answer

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, September can be a great choice for travel to San Juan Isla Grande Airport. Flights to San Juan Isla Grande Airport from Chicago in September are about $388 on average during September, but can be found for as low as $138.

Question 8

What is the cheapest time of day to fly from CHI to SIG?

Accepted Answer

One of the essential ways to save on airfare from Chicago to San Juan Isla Grande Airport is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 33% on airfare.

Question 9

Can I find deals for flights from Chicago to Isla Grande that include hotel bookings?

Accepted Answer

Yes. In addition to deals on Chicago to Isla Grande flights, Cheapflights offers vacation packages that include both flights and hotel.

Question 10

How can I find direct flights from Chicago to Isla Grande?

Accepted Answer

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Isla Grande.

Question 11

Can I find deals for business class flights from Chicago to Isla Grande?

Accepted Answer

Yes. Cheapflights offers flight deals from Chicago to Isla Grande by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Popular in	December
Cheapest in	September
Average price	$399

Cheap flights from Chicago (CHI) to Isla Grande (SIG)

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Everything you need to know about your flight from Chicago to San Juan Isla Grande Airport

What is the cheapest time of day to fly from CHI to SIG?

Find hourly flight availability from Chicago to Isla Grande. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

Reviews of airlines servicing Isla Grande

Read reviews from past customers who have flown United Airlines and Spirit Airlines from Chicago to San Juan Isla Grande Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Isla Grande. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

Can I find deals for flights from Chicago to Isla Grande that include hotel bookings?

How can I find direct flights from Chicago to Isla Grande?

Can I find deals for business class flights from Chicago to Isla Grande?

What is the cheapest month to book a flight from Chicago to San Juan Isla Grande Airport?

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