CHI - SIG

Find cheap flights from Chicago to San Juan Isla Grande

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KAYAK searches hundreds of travel sites at once for deals on flights to San Juan Isla Grande Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Juan, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Chicago to Isla Grande

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Isla Grande that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to San Juan

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to San Juan.
Discover the best prices for you by selecting your travel dates on KAYAK.
Multiple Airlines Logo
CHI-SIG
2053 mimulti-stop
Multiple Airlines Logo
SIG-CHI
2053 mimulti-stop
Multiple Airlines
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Useful Info

KAYAK's insights & trends for Chicago to San Juan flights

Get data-powered insights and trends into flights from Chicago to San Juan to help you find the cheapest flights, the best time to fly and much more.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San Juan Isla Grande Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to San Juan Isla Grande Airport is October, where tickets cost $134 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $784 and $359 respectively.

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Good to know

Low seasonSeptember
High seasonJune
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 1% lower on average.

When to book flights from Chicago to San Juan

Are your dates flexible? Find out the best times to travel from Chicago to San Juan based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to San Juan Isla Grande flights

  • Do I need a passport to fly between Chicago and San Juan Isla Grande?

    Yes, you’ll need a passport to travel to San Juan Isla Grande from Chicago.

  • Which aircraft models fly most regularly from Chicago to San Juan Isla Grande?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Chicago to San Juan Isla Grande?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to San Juan Isla Grande.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to San Juan Isla Grande?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Juan Isla Grande from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to San Juan Isla Grande?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Juan Isla Grande with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to San Juan Isla Grande?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Juan Isla Grande from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top airline flying from Chicago to San Juan

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Juan. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to San Juan? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
6.3
Spirit AirlinesOverall score based on 7961 reviews
5.1Food
5.9Comfort
7.1Crew
5.0Entertainment
6.6Boarding
Airline reviews

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

2.0 MediocreStephanie, Apr 2025ORD - LAX
Read more Spirit Airlines reviews

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

Amazing flying experience, even in not the best of weather. The staff made us comfortable and the flight was actually pretty smooth.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

It wasn’t a bad flight just very uncomfortable seating wise.

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

Everything you need to know for your flight from Chicago to San Juan

Information on your arrival and departure airports

Isla Grande (SIG)

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