ORD - POS

$220 Find Cheap Flights from Chicago to Port of Spain

This is the cheapest one-way 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 1/30. 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
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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 46,646,933 times on KAYAK, and here is why:

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Cheap Flight Deals from Chicago to Port of Spain (ORD-POS)

 
These are the cheapest deals for flights from Chicago to Port of Spain currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Port of Spain

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Port of Spain.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:50 am - 12:23 amORD-POS
13h 33m1 stop
1:30 am - 11:25 amPOS-ORD
11h 55m1 stop
$487United Airlines
Find Deal
Thu, Jan 16 - Sat, Jan 18
7:00 am - 11:14 pmORD-POS
14h 14m2 stops
4:35 pm - 12:27 amPOS-ORD
9h 52m1 stop
$492American Airlines
Find Deal
Thu, Jan 16 - Sun, Jan 19
7:56 am - 1:43 amORD-POS
16h 47m1 stop
2:16 pm - 12:21 amPOS-ORD
11h 05m1 stop
$493Copa Airlines
Find Deal
Fri, Apr 11 - Sat, Apr 19
6:54 pm - 2:03 pmORD-POS
18h 09m1 stop
3:18 pm - 12:23 pmPOS-ORD
22h 05m1 stop
$498American Airlines
Find Deal
Mon, Mar 10 - Tue, Mar 18
8:50 am - 12:23 amORD-POS
13h 33m1 stop
1:30 am - 10:14 amPOS-ORD
10h 44m1 stop
$505United Airlines
Find Deal
Thu, Jan 9 - Sun, Jan 12
8:05 am - 11:14 pmORD-POS
13h 09m2 stops
6:00 am - 7:22 pmPOS-ORD
15h 22m2 stops
$527American Airlines
Find Deal
Thu, Jan 9 - Mon, Jan 13
3:22 pm - 8:00 pmORD-POS
26h 38m1 stop
3:36 am - 10:27 pmPOS-ORD
20h 51m2 stops
Thu, Jan 16 - Sat, Jan 18
8:25 pm - 2:03 pmORD-POS
16h 38m2 stops
3:18 pm - 7:29 amPOS-ORD
17h 11m2 stops
$562American Airlines
Find Deal
Mon, Mar 10 - Tue, Mar 18
7:55 am - 1:41 amORD-POS
16h 46m1 stop
2:16 pm - 12:21 amPOS-ORD
11h 05m1 stop
$571Copa Airlines
Find Deal
Fri, Mar 28 - Fri, Apr 4
10:14 am - 2:41 amORD-POS
14h 27m1 stop
10:05 pm - 9:18 amPOS-ORD
13h 13m1 stop
$645JetBlue
Find Deal
Tue, Dec 10 - Tue, Dec 17

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 Tuesday. On your return trip to Chicago, you should consider flying back on a Sunday, and avoid Saturdays 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 $477 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $856 and $837 respectively.

Good to know

Low season

December

High season

March

Cheapest flight

$220
Best time to beat the crowds but there is an average 18% increase in price.
Most popular time to fly with an average 32% 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 $220 for a one-way ticket and $487 for a round-trip.

  • 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 $555 and an overall rating of 7.7, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $637 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.
7.7
Copa AirlinesOverall score based on 1779 reviews
7.1Food
7.0Entertainment
7.9Boarding
8.2Crew
7.5Comfort
Airline reviews

The flight was 6 hours delayed due to equipment problems, I had to spend my night in the airport terminal in tight quarters. A bag of chips was all they offered, Then I missed my connecting flight and waited another 2 hours. All in all that trip took me almost one day.

4.0 OkayKlaus, Nov 2024JFK - PTY
Read more Copa Airlines reviews

The flight was 6 hours delayed due to equipment problems, I had to spend my night in the airport terminal in tight quarters. A bag of chips was all they offered, Then I missed my connecting flight and waited another 2 hours. All in all that trip took me almost one day.

I like that they served a mail, I’m not sure about the in-flight entertainment. I didn’t really check. staff helped me with my luggage. Smooth boarding smooth takeoff smooth flight

It's the first time I couldn't check in online because they told me I had to call because there was a problem. Despite having called twice, I had to check in at the airport

Copa definitely offers better service and price than other airlines.

This airline doesn’t five and dime you for everything. I do think that a checked bag should be included in every fare.

The seats had plenty of leg room and the staff were very nice.

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.

No boarding announcements leading to the usual confusion and people trying to board before their group number.

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

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

Poor and identical to the first two legs, except for the crew who were patient, professional and of pleasant and jovial disposition!

We were delayed because of ground crew, not because the plane wasn’t ready to go. The food was better than usual!

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

United needs to figure out its Economy PLUS standards; its better than economy but that's not saying much. It seems like United stripped away all the basics for an international flight (such as In Seat entertainment) and repackaged some of them as plus. Would not fly United internationally again.

The flight was bumpy. No Breakfast or coffee was served, not even a bottle of water. The food was okay but odd. Rice with peas instead of couscous with some unknown green thing. United Airlines did not tell me that there was VERY LIMITED HANDICAP SERVICE IN NAPLES. De-plane via 20 aluminum steps. Taken to Van. You must walk into the terminal, find luggage, and then walk out to the rental car pickup spot that is 1 block from the terminal.

Crew did their best but the plane configuration is too tight if you're bigger than an average sardine. Controls for the entertainment system didn't all work. The aircraft hadn't been cleaned in awhile.

Flight was delayed due to weather and clogged toilet. Had to deplane. Flight was 3 hours delayed. Crew was awesome and offered water and snacks.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

WiFi was not working from pos to Mia…. As well as they rushed us to the gate as if the flight was already here and leaving shortly when the plane never even arrived and took off until the scheduled time so then why rush us to the gate and have us thinking we will miss our flight.

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

The main problem was delay. The plane was at the gate early and bags were loaded. However, there was no crew for the flight. They were inbound from LGA and had to land and make their way to our gate. It took more than 40 minutes. Then, once the crew arrived and boarded, one of the crew members had to deplane and then a replacement crew member had to be found. It took another 40 minutes or so to get the final crew member. In all, we took off about 2 hours later than our scheduled departure time. Once in the air, the flight was great. Smooth most of the way. The crew was professional and efficient.

Book cheap flights from Chicago to Port of Spain

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Port of Spain found on KAYAK in the last 72 hours.
1/30Thu
2 stopsAmerican Airlines
13h 09mORD-POS
$220
3/9Sun
1 stopCopa Airlines
9h 37mORD-POS
$262
3/8Sat
1 stopUnited Airlines
13h 08mORD-POS
$265
12/28Sat
1 stop
23h 09mORD-POS
$276
12/27Fri
2 stops
38h 34mORD-POS
$296
3/9Sun
2 stopsAmerican Airlines
16h 38mORD-POS
$308
3/8Sat
2 stopsAmerican Airlines
15h 38mORD-POS
$341
12/27Fri
1 stopUnited Airlines
24h 54mORD-POS
$451
3/8Sat
3 stopsTurkish Airlines
35h 46mORD-POS
$1,461
1/30Thu
3 stopsTurkish Airlines
35h 38mORD-POS
$1,870

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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.
11/24Sun
multi-stop
22h 21mORD-POS
11/26Tue
multi-stop
24h 14mPOS-ORD
$629
11/25Mon
multi-stop
22h 15mORD-POS
11/27Wed
multi-stop
20h 37mPOS-ORD
$656
11/24Sun
multi-stop
25h 15mORD-POS
11/26Tue
multi-stop
10h 36mPOS-ORD
$740
11/24Sun
multi-stop
25h 15mORD-POS
11/26Tue
multi-stop
10h 36mPOS-ORD
$784
11/25Mon
multi-stopUnited Airlines
14h 48mORD-POS
11/26Tue
multi-stopUnited Airlines
10h 32mPOS-ORD
$947
11/23Sat
multi-stopAmerican Airlines
8h 07mORD-POS
11/30Sat
multi-stopAmerican Airlines
18h 47mPOS-ORD
$987
11/23Sat
multi-stopAmerican Airlines
10h 19mORD-POS
11/30Sat
multi-stopAmerican Airlines
16h 44mPOS-ORD
$992
11/24Sun
multi-stopUnited Airlines
9h 38mORD-POS
11/25Mon
multi-stopUnited Airlines
17h 31mPOS-ORD
$1,027
11/23Sat
multi-stopUnited Airlines
26h 23mORD-POS
11/29Fri
multi-stopUnited Airlines
13h 01mPOS-ORD
$1,117
11/25Mon
multi-stopUnited Airlines
13h 35mORD-POS
11/26Tue
multi-stopUnited Airlines
15h 24mPOS-ORD
$9,112

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Everything you need to know for your flight from Chicago to Port of Spain

Information on your arrival and departure airports

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