Find flights
Deals
Insights
When to book
FAQs & Tips
Airlines

ORD - POS

$353 Find cheap flights from Chicago to Port of Spain

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Port of Spain departing on 7/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/8
Sat 6/15

Search hundreds of travel sites at once for deals on flights to Port of Spain

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Port of Spain, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Port of Spain, as well as popular online travel agencies
In the last 7 days travelers have searched 43,968,530 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Chicago to Port of Spain (ORD-POS)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Port of Spain that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:56 pm - 2:02 pmORD-POS
19h 06m2 stops
3:14 pm - 1:11 pmPOS-ORD
22h 57m2 stops
$353Frontier
Find Deal
Thu, Jul 11 - Fri, Jul 19
5:56 pm - 2:02 pmORD-POS
19h 06m2 stops
3:14 pm - 9:08 amPOS-ORD
18h 54m2 stops
$366Frontier
Find Deal
Wed, Sep 18 - Sun, Sep 22
11:50 am - 9:19 pmORD-POS
8h 29m1 stop
3:18 pm - 11:34 pmPOS-ORD
9h 16m1 stop
$427American Airlines
Find Deal
Thu, Sep 19 - Mon, Sep 23
8:20 am - 9:19 pmORD-POS
11h 59m2 stops
7:58 am - 8:11 pmPOS-ORD
13h 13m2 stops
$431American Airlines
Find Deal
Thu, Sep 19 - Mon, Sep 23
7:56 am - 1:17 pmORD-POS
28h 21m1 stop
4:09 am - 1:18 pmPOS-ORD
10h 09m1 stop
$451Copa Airlines
Find Deal
Thu, Aug 22 - Wed, Aug 28
8:50 pm - 6:55 pmORD-POS
21h 05m1 stop
2:20 pm - 9:04 amPOS-ORD
19h 44m2 stops
Tue, Jun 11 - Wed, Jun 19
5:34 pm - 6:55 pmORD-POS
24h 21m1 stop
2:20 pm - 9:04 amPOS-ORD
19h 44m2 stops
Mon, Jun 10 - Wed, Jun 19
7:10 am - 11:23 pmORD-POS
15h 13m1 stop
12:30 am - 10:53 amPOS-ORD
11h 23m1 stop
$517United Airlines
Find Deal
Mon, Jun 10 - Tue, Jun 18
10:35 am - 11:23 pmORD-POS
11h 48m1 stop
12:30 am - 12:52 pmPOS-ORD
13h 22m1 stop
$533United Airlines
Find Deal
Wed, Sep 18 - Mon, Sep 23
3:10 pm - 1:42 amORD-POS
9h 32m1 stop
4:09 am - 1:18 pmPOS-ORD
10h 09m1 stop
$557Copa Airlines
Find Deal
Wed, Jul 3 - Thu, Jul 11

Flights from Chicago to Port of Spain - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Port of Spain to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Port of Spain?

The average price of all flights from Chicago O'Hare Intl Airport to Port of Spain clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Port of Spain on a Sunday and more expensive on a Saturday. On your return trip to Chicago, you should consider flying back on a Wednesday, and avoid Mondays for better deals.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Port of Spain?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago O'Hare Intl Airport to Port of Spain, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago O'Hare Intl Airport to Port of Spain is January, where tickets cost $493 on average. On the other hand, the most expensive months are November and December, where the average cost of tickets is $1,024 and $942 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Port of Spain?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to Port of Spain, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago O'Hare Intl Airport to Port of Spain, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 85 days before departure.

Good to know

Low season

January

High season

March

Cheapest flight

$353
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago to Port of Spain

When to book flights from Chicago to Port of Spain

Are your dates flexible? Find out the best times to travel from Chicago to Port of Spain based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Port of Spain flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Port of Spain?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Port of Spain was $353 for a round-trip ticket.

  • Do I need a passport to fly between Chicago and Port of Spain?

    Yes

  • Which airports will I be using when flying from Chicago to Port of Spain?

    When flying out of Chicago you will be using Chicago O'Hare Intl. You will be landing at Port of Spain, also known as Port of Spain Piarco Intl.

  • Which aircraft models fly most regularly from Chicago to Port of Spain?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Port of Spain?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Port of Spain, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Port of Spain, Copa Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Port of Spain are Copa Airlines and United Airlines. With an average price for the route of $532 and an overall rating of 7.8, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $664 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago to Port of Spain?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Port of Spain.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Port of Spain?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Port of Spain from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Port of Spain?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Port of Spain with an airline and back to Chicago with another airline. Booking your flights between Chicago and POS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Port of Spain?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Port of Spain from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 3 airlines serving from Chicago to Port of Spain

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Port of Spain. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Port of Spain? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
Copa AirlinesOverall score based on 2766 reviews
7.7Comfort
7.3Food
8.3Crew
7.2Entertainment
8.1Boarding
Airline reviews

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

8.0 ExcellentAntonio, Mar 2024LAX - PTY
Read more about Copa Airlines reviews

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

Left my bags in origin city on a business class ticket , spent about 2-3 days in the same clothes plus the flight .

the planes are not modern there are no phone chargers

As usual, the flight with normal legroom was not very comfortable, but the second flight was much better because we had paid for extra legroom. It was very nice to check our bags without an extra fee.

LOCKED MY BAG WITHOUT CONSENT. Had to have my zippers cut upon arrival in Costa Rica.

Pros: "The seats in economy were confortable. The best thing was Copa gave us seats in the second line and my family traveled together."
Cons: "Coffe service could better the experience"
Pros: "The crew was very interested on help and attentive with the passengers. But the seat wasn't comfortable. The design of the cushion is not the best to be seating"
Pros: "You were on time, that is the most important thing in a fly"
Cons: "You could improve your entertainment, you are not a cheap company"
Pros: "That there was seltzer"
Cons: "The management of preparing the flight and plane so that it was ready for the trip!!"
Pros: "Copa was convenient and easy. Very easy boarding process and I appreciated the day flight."
Cons: "This is a business class that is equivalent to a US carrier domestic first class. Good seats, not lay flat but wide on my 737-800. The food and service emulated say American Airlines Domestic 1C as well. Everything was just good enough, and much cheaper that international business on the majors."

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Last minute flights from Chicago to Port of Spain

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Port of Spain that are departing in the next 10 days.
5/10Fri
multi-stop
12h 20mORD-POS
6/10Mon
multi-stop
29h 16mPOS-ORD
$658
5/10Fri
multi-stopUnited Airlines
11h 38mORD-POS
6/9Sun
multi-stopUnited Airlines
23h 29mPOS-ORD
$675
5/10Fri
multi-stopAmerican Airlines
18h 25mORD-POS
6/10Mon
multi-stopAmerican Airlines
18h 40mPOS-ORD
$690
5/10Fri
multi-stopAmerican Airlines
14h 04mORD-POS
6/10Mon
multi-stopAmerican Airlines
15h 37mPOS-ORD
$773
5/10Fri
multi-stop
29h 50mORD-POS
6/10Mon
multi-stop
23h 24mPOS-ORD
$799
5/10Fri
multi-stop
29h 50mORD-POS
6/10Mon
multi-stop
28h 30mPOS-ORD
$823
5/11Sat
multi-stopUnited Airlines
14h 53mORD-POS
5/14Tue
multi-stopUnited Airlines
10h 00mPOS-ORD
$936
5/11Sat
multi-stopUnited Airlines
14h 53mORD-POS
5/14Tue
multi-stopUnited Airlines
15h 12mPOS-ORD
$937
5/11Sat
multi-stopAmerican Airlines
8h 10mORD-POS
5/15Wed
multi-stopAmerican Airlines
10h 10mPOS-ORD
$942
5/11Sat
multi-stopAmerican Airlines
13h 04mORD-POS
5/15Wed
multi-stopAmerican Airlines
13h 40mPOS-ORD
$943

Search by stops

Search by airline

Search by price

Chicago - Port of Spain Flights

Departure:

Chicago (undefined)United States

Destination:

Port of Spain (POS)Trinidad and Tobago

Return flight deals:

Port of Spain - Chicago

Cabin classes: