Cheap Flights from Chicago to Aguadilla from $313 Return

Flight deals from Chicago to Aguadilla

Looking for cheap tickets from Chicago to Aguadilla, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.

Aguadilla.$313 per passenger.Departing Wed, 25 Feb, returning Wed, 11 Mar.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed, 25 Feb, arriving in Aguadilla.Inbound indirect flight with Frontier Airlines, departs from Aguadilla on Wed, 11 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From $313, select.

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Flying from Chicago to Aguadilla

Arm yourself with these facts on the fly.

Cheapest flight found	$313
Cheapest month to fly	February
Cheapest airport to fly from	Chicago O'Hare International

How to find cheap flights from Chicago to Aguadilla

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Aguadilla. Other savvy travellers recently found return flights from $313 and one-way tickets from $168 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into Aguadilla

At the moment, the lowest priced flight tickets to Aguadilla are from Chicago O'Hare International Airport to Aguadilla Airport.

Fly in February

We crunched the flight calendar and found the cheapest time to fly from Chicago to Aguadilla is currently February.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Aguadilla.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Aguadilla go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Aguadilla to Aguadilla flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Aguadilla flight price?

We looked at all of the upcoming return flights from Chicago to Aguadilla we could find over the next 12 months. It looks like $313 is the best price. This is good, compared to the average Aguadilla ticket price of $313.

What is the cheapest month to fly from Chicago to Aguadilla?

The cheapest month to fly from Chicago to Aguadilla is currently February.

Which upcoming date is cheapest to fly from Chicago to Aguadilla on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Aguadilla on Wednesday, 25 February 2026.

Are there any direct flights from Chicago to Aguadilla?

Currently, there aren't any direct flights from Chicago to Aguadilla, but you can still fly with a stopover.

If I'm flying from Chicago, where in Aguadilla is cheapest to fly into?

If you're flying from Chicago, the cheapest city in Aguadilla to fly into is Aguadilla. The cheapest airport serving Aguadilla at the moment is Aguadilla.