Cheap Flights from Chicago O'Hare International Airport to San Juan/Laventille from $901 Return

Flight deals from Chicago O'Hare International Airport to San Juan/Laventille

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International Airport to San Juan/Laventille? If you want to travel next month, return fares start from $940. Find the lowest prices on one-way and return tickets right here.

Port Of Spain.$901 per passenger.Departing Sat, 3 Oct, returning Sat, 10 Oct.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sat, 3 Oct, arriving in Port Of Spain.Inbound indirect flight with Air Canada, departs from Port Of Spain on Sat, 10 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $901, select.

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Flying from Chicago O'Hare International Airport to San Juan/Laventille

Arm yourself with these facts on the fly.

Cheapest flight found	$901
Cheapest month to fly	October

How to find cheap flights from Chicago O'Hare International Airport to San Juan/Laventille

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago O'Hare International Airport to San Juan/Laventille. Other savvy travellers recently found return flights from $901 and one-way tickets from $451. Ready to join them? Here are a few tips to help you do it the smart way.

Fly in October

The cheapest time to fly from Chicago O'Hare International Airport to San Juan/Laventille is currently October.

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 O'Hare International Airport to anywhere you choose in San Juan/Laventille.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago O'Hare International Airport to your chosen airport in San Juan/Laventille 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 San Juan/Laventille Airport to San Juan/Laventille flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What is the average price of a flight from Chicago O'Hare International Airport to San Juan/Laventille?

We looked at all of the upcoming return flights from Chicago O'Hare International Airport to San Juan/Laventille we could find over the next 12 months. It looks like $901 is the best price. This is good, compared to the average San Juan/Laventille ticket price of $901.

What is the cheapest month to fly from Chicago O'Hare International Airport to San Juan/Laventille?

The cheapest month to fly from Chicago O'Hare International Airport to San Juan/Laventille is currently October.

Which upcoming date is cheapest to fly from Chicago O'Hare International Airport to San Juan/Laventille on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago O'Hare International Airport to San Juan/Laventille on Saturday, 3 October 2026.

If I'm flying from Chicago O'Hare International Airport, where in San Juan/Laventille is cheapest to fly into?

If you're flying from Chicago O'Hare International, the cheapest city in San Juan/Laventille to fly into is Port Of Spain. The cheapest airport serving Port Of Spain at the moment is Port Of Spain.