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Find cheap flights from Chicago to Trinidad and Tobago from $440

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 Trinidad and Tobago departing on 5/15. 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
Wed 6/5
Wed 6/12

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Best Trinidad and Tobago Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Port of Spain
Port of Spain1 stop$440

Good to know

Low season

January

High season

March

Cheapest flight

$440
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

FAQs - booking Trinidad and Tobago flights

  • How does KAYAK find such low prices on flights from Chicago to Trinidad and Tobago?

    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 Trinidad and Tobago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Trinidad and Tobago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Trinidad and Tobago 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 Trinidad and Tobago?

    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 Trinidad and Tobago with an airline and back to Chicago with another airline.

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

    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 Trinidad and Tobago 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 tips for finding cheap flights to Trinidad and Tobago

  • Morning departure is around 68% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Chicago to Trinidad and Tobago

 
Need help choosing which airline to fly with from Chicago to Trinidad and Tobago? 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 2791 reviews
7.3Food
7.2Entertainment
7.7Comfort
8.1Boarding
8.3Crew
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."

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.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

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.

Book cheap flights from Chicago to Trinidad and Tobago

Recent round-trip flight deals

5/15Wed
1 stop
20h 40mORD-POS
6/4Tue
2 stops
30h 56mPOS-ORD
$440
5/18Sat
1 stop
20h 20mORD-POS
6/4Tue
2 stops
20h 24mPOS-ORD
$454
5/15Wed
2 stops
27h 27mORD-POS
6/5Wed
1 stop
9h 15mPOS-ORD
$460
5/18Sat
1 stop
20h 20mORD-POS
6/3Mon
2 stops
20h 24mPOS-ORD
$462
5/15Wed
1 stop
20h 40mORD-POS
6/6Thu
2 stops
13h 39mPOS-ORD
$467
5/18Sat
1 stopAmerican Airlines
13h 34mORD-POS
6/4Tue
1 stopAmerican Airlines
18h 46mPOS-ORD
$560
5/18Sat
2 stopsAmerican Airlines
10h 39mORD-POS
6/4Tue
2 stopsAmerican Airlines
15h 54mPOS-ORD
$563
5/17Fri
1 stopUnited Airlines
24h 46mORD-POS
6/2Sun
1 stopUnited Airlines
11h 23mPOS-ORD
$618
5/20Mon
1 stopUnited Airlines
13h 38mORD-POS
6/3Mon
1 stopUnited Airlines
13h 21mPOS-ORD
$627
6/20Thu
1 stopBritish Airways
18h 26mORD-POS
6/26Wed
1 stopBritish Airways
18h 40mPOS-ORD
$1,485

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Last minute flights from Chicago to Trinidad and Tobago

Last minute flight, train and bus deals

5/11Sat
multi-stop
24h 20mORD-POS
5/14Tue
multi-stop
29h 40mPOS-ORD
$556
5/11Sat
multi-stop
24h 20mORD-POS
5/15Wed
multi-stop
20h 24mPOS-ORD
$637
5/11Sat
multi-stop
23h 53mORD-POS
5/15Wed
multi-stop
15h 32mPOS-ORD
$677
5/11Sat
multi-stop
23h 47mORD-POS
5/15Wed
multi-stop
15h 32mPOS-ORD
$691
5/11Sat
multi-stop
23h 53mORD-POS
5/14Tue
multi-stop
20h 24mPOS-ORD
$693
5/11Sat
multi-stopUnited Airlines
14h 53mORD-POS
5/14Tue
multi-stopUnited Airlines
15h 12mPOS-ORD
$877
5/11Sat
multi-stopJetBlue
10h 43mORD-POS
5/15Wed
multi-stopJetBlue
11h 08mPOS-ORD
$879
5/11Sat
multi-stopUnited Airlines
14h 53mORD-POS
5/13Mon
multi-stopUnited Airlines
10h 00mPOS-ORD
$937
5/11Sat
multi-stopAmerican Airlines
15h 19mORD-POS
5/15Wed
multi-stopAmerican Airlines
13h 40mPOS-ORD
$938
5/11Sat
multi-stopAmerican Airlines
8h 10mORD-POS
5/15Wed
multi-stopAmerican Airlines
13h 40mPOS-ORD
$940

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Chicago - Trinidad and Tobago Flights

Departure:

Chicago (ORD)United States

Return flight deals:

Trinidad and Tobago - Chicago

Cabin classes: