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Isla Grande

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

CHI — SIG
oct. 29 — nov. 51
mié. 10/29
mié. 11/5
1 adult, Economy
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Cheap flight deals from Chicago to Isla Grande

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Isla Grande (SIG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated septiembre 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

October

Average price

$381
Provider with most accurate pricing for Chicago (CHI)-San Juan Isla Grande flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San Juan Isla Grande flights.
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Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Compare providers for flights from Chicago to Isla Grande

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Isla Grande in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-San Juan Isla Grande Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San Juan Isla Grande Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San Juan Isla Grande Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-San Juan Isla Grande Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San Juan Isla Grande Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Isla Grande

Have a flexible travel schedule? Discover the best time to fly to Isla Grande from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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 septiembre 29, 2025.

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.

Reviews of airlines servicing Isla Grande

Get insights into the airlines that provide service to Isla Grande. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isla Grande. Reviews last updated septiembre 29, 2025.
Read reviews from past customers who have flown United 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.
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Boarding

7.7

Entertainment

7.1

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

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?

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

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

    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.

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

    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.

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

    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.

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