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388 € Cheap Flights from Chicago to Port Of Spain

Compare Chicago to Port Of Spain flight deals

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Flight deals from Chicago to Port Of Spain

Looking for a cheap last-minute deal or the best return flight from Chicago to Port Of Spain Airport? If you want to travel next month, return fares start from 388 €. Find the lowest prices on one-way and return tickets right here.
Port Of Spain.388 € per passenger.Departing Mon, 1 Jun, returning Tue, 9 Jun.Return flight with Frontier Airlines and Caribbean Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 1 Jun, arriving in Port Of Spain.Inbound indirect flight with Caribbean Airlines, departs from Port Of Spain on Tue, 9 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From 388 €, select.
Port Of Spain.393 € per passenger.Departing Thu, 28 May, returning Mon, 1 Jun.Return flight with Frontier Airlines and Caribbean Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu, 28 May, arriving in Port Of Spain.Inbound indirect flight with Caribbean Airlines, departs from Port Of Spain on Mon, 1 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From 393 €, select.
Port Of Spain.490 € per passenger.Departing Thu, 11 Jun, returning Tue, 7 Jul.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Thu, 11 Jun, arriving in Port Of Spain.Inbound indirect flight with Air Canada, departs from Port Of Spain on Tue, 7 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 490 €, select.
Port Of Spain.514 € per passenger.Departing Thu, 26 Nov, returning Fri, 18 Dec.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Thu, 26 Nov, arriving in Port Of Spain.Inbound indirect flight with Air Canada, departs from Port Of Spain on Fri, 18 Dec, arriving in Chicago O'Hare International.Price includes taxes and charges.From 514 €, select.
Port Of Spain.516 € per passenger.Departing Fri, 3 Jul, returning Mon, 6 Jul.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 3 Jul, arriving in Port Of Spain.Inbound indirect flight with Air Canada, departs from Port Of Spain on Mon, 6 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From 516 €, select.
Port Of Spain.517 € per passenger.Departing Fri, 14 Aug, returning Mon, 24 Aug.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 14 Aug, arriving in Port Of Spain.Inbound indirect flight with Air Canada, departs from Port Of Spain on Mon, 24 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From 517 €, select.
Port Of Spain.525 € per passenger.Departing Wed, 20 Jan, returning Mon, 25 Jan.Return flight with Copa.Outbound indirect flight with Copa, departs from Chicago O'Hare International on Wed, 20 Jan, arriving in Port Of Spain.Inbound indirect flight with Copa, departs from Port Of Spain on Mon, 25 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 525 €, select.
Port Of Spain.590 € per passenger.Departing Wed, 20 May, returning Sun, 31 May.Return flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Wed, 20 May, arriving in Port Of Spain.Inbound indirect flight with United, departs from Port Of Spain on Sun, 31 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From 590 €, select.
Port Of Spain.925 € per passenger.Departing Fri, 26 Mar, returning Mon, 29 Mar.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Chicago O'Hare International on Fri, 26 Mar, arriving in Port Of Spain.Inbound indirect flight with Air Canada, departs from Port Of Spain on Mon, 29 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From 925 €, select.
Port Of Spain.1.205 € per passenger.Departing Thu, 29 Oct, returning Tue, 3 Nov.Return flight with WestJet and Caribbean Airlines.Outbound indirect flight with WestJet, departs from Chicago Midway on Thu, 29 Oct, arriving in Port Of Spain.Inbound indirect flight with Caribbean Airlines, departs from Port Of Spain on Tue, 3 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 1.205 €, select.
Port Of Spain.1.382 € per passenger.Departing Sat, 19 Dec, returning Sat, 2 Jan.Return flight with Arajet and Caribbean Airlines.Outbound indirect flight with Arajet, departs from Chicago O'Hare International on Sat, 19 Dec, arriving in Port Of Spain.Inbound indirect flight with Caribbean Airlines, departs from Port Of Spain on Sat, 2 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From 1.382 €, select.

Find the cheapest month to fly from Chicago to Port Of Spain

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago to Port Of Spain flights are currently cheapest in June.
May
from 590 €
Jun
from 388 €
Jul
from 516 €
Aug
from 517 €
Sep
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Oct
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Nov
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Dec
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Jan
from 525 €
Feb
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Mar
from 925 €
Apr
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Chicago to Port Of Spain: Alternative routes

Compare routes from Chicago to Port Of Spain below. You may find an airport to fly into that's cheaper, faster, or easier than Port Of Spain.

Port Of Spain

20km from central Port Of Spain
ClosestCheapest
from 388 €
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Chicago to Port Of Spain: Flight information

The things to know before you go.
Cheapest flight found388 €
Cheapest month to flyJune

Finding cheap flights from Chicago to Port Of Spain: Frequently asked questions

The best price we found for a return flight from Chicago to Port Of Spain is 388 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Chicago to Port Of Spain. But we found flights with one stop from 388 €.
As of May 2026, there are no flights flying from Chicago to Port Of Spain.
The cheapest month to fly from Chicago to Port Of Spain is usually June.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Port Of Spain Airport on Monday, 1 June 2026.
No airlines currently offer direct flights between Chicago and Port Of Spain Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Port Of Spain but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Port Of Spain is around 40 days in advance, so don’t leave your flight to the last minute.
The cheapest airline that flies to Port Of Spain is Frontier Airlines .

Travelling from Chicago to Piarco International Airport (POS): What you need to know

  • Chicago has a couple of airports where you can kick off your travels. Check out your options for booking a flight from Chicago to Piarco International Airport (POS) heading out from O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).

  • The timezone in Port Of Spain is UTC-4, which is one hour ahead of Chicago. Piarco International Airport is located in Port Of Spain.

  • Leave enough time to catch your flight from Chicago to POS. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Delays at security and check-in are more likely if you're flying during high season, so give yourself a bit more breathing room. The recommendation for peak periods? Get there up to four hours ahead for international flights and two hours for domestic departures.

Airports in Chicago

O'Hare International Airport (ORD)

  • Think about adding a stopover to find cheap flights from Chicago to POS. Just deselect 'Direct flights only' when searching for departures from O'Hare International Airport (ORD). Take a break from travelling at one of these popular airports:

    • Miami International Airport (MIA)

    • Fort Lauderdale-Hollywood International Airport (FLL)

    • Princess Juliana International Airport (SXM)

  • Located around 40 kilometres from central Chicago, ORD can be reached in about 35 minutes by car (depending on traffic). The journey on public transport takes roughly 55 minutes.

  • In search of a comfortable hotel close to O'Hare International Airport? If you're catching an early flight from Chicago to Piarco International Airport, these accommodation options will have you sleeping conveniently close to check-in:

  • 74.85% of flights departing from O'Hare International Airport touch down at their destination on time.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Get the most out of your holiday with a stopover on your flight from Chicago to Piarco International Airport. Check out these connections between Chicago Midway International Airport and POS:

    • Miami International Airport (MIA)

    • Orlando International Airport (MCO)

    • Fort Lauderdale-Hollywood International Airport (FLL)

  • MDW is around 19 kilometres from central Chicago. It'll take 20 minutes or so to get to the airport driving from the city centre. Public transport takes approximately 45 minutes.

  • Get your holiday started early with an additional night away from home. Before your Chicago to POS flight, unwind in one of these hotels close to Chicago Midway International Airport:

  • Chicago Midway International Airport has an on-time performance rate of 77.88%. This figure gives an insight into how frequently flights that take off from this airport land at their destination on schedule.

  • You'll find MDW at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • The journey to RFD from the centre of Chicago is around 4 hours 15 minutes on public transport. If you're in a car, it'll take you about 1 hour 25 minutes to cover the 137 kilometres or so.

  • Make catching an early Chicago to Piarco International Airport flight the easiest part of your trip. Stay at one of these accommodation options near Chicago Rockford International Airport and get to your departure gate with time to spare:

  • Flights that take off from RFD arrive at their destination within the scheduled time frame 76.19% of the time.

  • You'll find Chicago Rockford International Airport at 2 Airport Cir.

About Piarco International Airport (POS)

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Chicago to Piarco International Airport. Book one of these accommodation options near POS instead:

  • Pick up a Piarco International Airport rental car and explore Port Of Spain and beyond with your own wheels. Sixt, Alamo and Ace Rent a Car are leading providers to choose from here.

  • Lock in the lowest price by reserving your vehicle around one week before your Chicago to Piarco International Airport flight.

How to find the cheapest flights from Chicago to Piarco International Airport (POS)

  • 208 € is the lowest price for a one-way ticket from Chicago to Piarco International Airport. A return flight starts from 388 €. These prices may change depending on demand.

  • Booking ahead of time is often the key to scoring a cheap flight from Chicago to POS. Flight prices rise as demand increases, so the closer you get to departure, the more you'll likely spend.

  • If you're flexible with your travel plans, use the 'Whole month' search tool. It'll give you the lowest price in each month when searching for your Chicago to Piarco International Airport ticket.

  • Finding a cheap plane ticket from Chicago to POS is a piece of cake with Price Alerts. All you need to do is create one of these automatic alerts and we'll let you know when there's a price drop.

  • Filters make it easier to track down a bargain for your flight from Chicago to Piarco International Airport. Choose the departure times, airlines and number of stops that make sense for you. Then sort the results by 'Cheapest' to find the most affordable option fast.

The best time to fly from Chicago to Piarco International Airport (POS)

  • July is when most people book flights from Chicago to Piarco International Airport (POS). Plan your visit to Port Of Spain in February for a more laid-back experience.

  • When booking your Chicago to POS plane ticket, consider what kind of weather you prefer. September is the warmest month in Port Of Spain, with temperatures ranging from 24ºC (75ºF) to 31ºC (88ºF).

  • If you like cooler conditions, look for a cheap ticket from Chicago to Piarco International Airport in February when temperatures are between 22ºC (72ºF) and 30ºC (86ºF).

More about Port Of Spain

  • After booking your flight from Chicago to Piarco International Airport, find a hotel that puts you in a great location. Make one of these options your base for exploring Port Of Spain:

  • There are so many things to see and do in this city, it can be tricky to work out where to begin. Blue Basin Waterfall, Holy Trinity Cathedral and Our Lady of Lourdes are top attractions which should be on any well-planned Port Of Spain itinerary.

Explore more of Trinidad and Tobago

  • Scarborough is just one of the many cities in Trinidad and Tobago waiting to be discovered once you've seen Port Of Spain. Around 97 kilometres away to the north-east, top sights here include Fort King George, Scarborough Botanical Garden and St. Andrews Anglican.

  • Journey 88 kilometres north-east from Port Of Spain and you'll reach Plymouth, another favourite stop in Trinidad and Tobago. Don't leave without experiencing Fort James (Fort Jacobus) and Mystery Tombstone.

Plan the rest of your trip from Chicago to Port Of Spain

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.