Cheap flights from Chicago to Port of Spain from $235
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Port of Spain departing on 7/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Chicago to Port of Spain
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest day to depart on your flight to Port of Spain?
The cheapest day to depart from Chicago to Port of Spain is on a Sunday when prices can be found for as low as $569. Flights from Chicago to Port of Spain on a Monday will generally be more expensive and average around $706. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.
What is the cheapest time of day to depart on your flight to Port of Spain?
In the afternoon is the cheapest time of day to fly from Chicago to Port of Spain when you can find flight prices for as low as $535. Flying to Port of Spain in the afternoon is an ideal time because this is during off-peak travel hours. In the evening is when there is more demand to fly to Port of Spain, so prices are often more expensive at around $847 per ticket.
When to book flights from Chicago to Port of Spain
Cheap Chicago to Port of Spain (CHI to POS) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Port of Spain
How far is Chicago to Port of Spain Piarco Intl by plane?
Port of Spain Piarco Intl is 2671.5 mi away from Chicago. 8h 00m is a normal flight duration for this route.
When did momondo last update prices for flights from Chicago to Port of Spain Piarco Intl Airport?
Prices for flights from Chicago to Port of Spain Piarco Intl Airport refresh daily.
How many operators does momondo search for flights from Chicago to Port of Spain Piarco Intl Airport?
As of June 2025, there are 2 operators available to choose from for flights from Chicago to Port of Spain Piarco Intl Airport.
How old do you have to be to fly from Chicago to Port of Spain Piarco Intl Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Port of Spain Piarco Intl Airport.
What documentation or ID do you need to fly to Port of Spain Piarco Intl Airport?
The travel and health documents required for your trip to Port of Spain Piarco Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Port of Spain Piarco Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Chicago to Port of Spain?
Based on momondo bookings for flights between Chicago and Port of Spain, the leading airline is American Airlines, making up 54% of the total bookings. Other popular airlines include United Airlines with 46%.
Best airlines flying from Chicago to Port of Spain
Compare and see reviews for airlines that fly from Chicago to Port of Spain with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $480 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $487 | Free Cancellation | Rating 7.2 10,000 reviews |
Traveling to a place near Port of Spain?
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Why should I use momondo to find a flight deal from Chicago to Port of Spain?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Port of Spain. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Port of Spain with flexible booking policies on momondo?
Flights from Chicago to Port of Spain with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to Port of Spain?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Port of Spain from Chicago.
I’m not ready to book a flight from Chicago to Port of Spain right now. Can momondo alert me if prices change?
If you are simply researching potential flights to Port of Spain, momondo offers a useful price alert feature which will track prices for flights to Port of Spain from Chicago and alert you when they change.