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Find cheap flights from Chicago to Trinidad from $209

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 Trinidad departing on 8/6. 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
Thu 6/20
Thu 6/27

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Best Trinidad Flight Deals

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

Port of Spain
Port of Spain1 stop$513

Good to know

Low season

January

High season

March

Cheapest flight

$209
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 flights

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

    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.

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

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

    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 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?

    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 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 Trinidad

 
Need help choosing which airline to fly with from Chicago to Trinidad? 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 2672 reviews
7.3Food
7.2Entertainment
8.1Boarding
7.7Comfort
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."

Standard flight experience, but there is only power at the seat to row 20 on the aircraft, on my initial check in it did not say that was the case

Energetic crew - flight full of swiftied going to Taylor's opening show in Paris! Long lines for bathroom made out kind of suck though

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

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

Recent round-trip flight deals

6/19Wed
1 stop
21h 05mORD-POS
6/23Sun
2 stops
29h 59mPOS-ORD
$513
6/20Thu
1 stopUnited Airlines
15h 13mORD-POS
10/16Wed
1 stopUnited Airlines
11h 52mPOS-ORD
$517
6/25Tue
1 stopUnited Airlines
25h 38mORD-POS
11/25Mon
1 stopUnited Airlines
11h 47mPOS-ORD
$526
6/24Mon
2 stops
25h 49mORD-POS
6/29Sat
1 stop
12h 41mPOS-ORD
$596
6/19Wed
1 stop
23h 40mORD-POS
6/23Sun
1 stop
15h 45mPOS-ORD
$597
6/24Mon
1 stop
24h 21mORD-POS
6/29Sat
1 stop
11h 39mPOS-ORD
$616
6/20Thu
2 stopsAmerican Airlines
28h 46mORD-POS
10/17Thu
2 stopsAmerican Airlines
19h 52mPOS-ORD
$653
6/25Tue
1 stopAmerican Airlines
28h 54mORD-POS
11/26Tue
2 stopsAmerican Airlines
28h 59mPOS-ORD
$697
6/20Thu
2 stopsAmerican Airlines
28h 46mORD-POS
10/17Thu
2 stopsAmerican Airlines
21h 51mPOS-ORD
$698
6/25Tue
2 stopsAmerican Airlines
29h 51mORD-POS
11/26Tue
2 stopsAmerican Airlines
28h 59mPOS-ORD
$727

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Recent one-way flight deals

8/6Tue
2 stopsAmerican Airlines
14h 00mORD-POS
$209
8/6Tue
1 stopAmerican Airlines
14h 38mORD-POS
$210
8/6Tue
3 stops
30h 57mORD-POS
$270

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Last minute flights from Chicago to Trinidad

Last minute flight, train and bus deals

5/24Fri
multi-stop
24h 30mORD-POS
5/28Tue
multi-stop
24h 35mPOS-ORD
$881
5/24Fri
multi-stopUnited Airlines
13h 30mORD-POS
5/27Mon
multi-stopUnited Airlines
20h 08mPOS-ORD
$892
5/24Fri
multi-stopAmerican Airlines
12h 04mORD-POS
5/28Tue
multi-stopAmerican Airlines
18h 53mPOS-ORD
$960
5/24Fri
multi-stop
24h 30mORD-POS
5/28Tue
multi-stop
29h 49mPOS-ORD
$974
5/24Fri
multi-stop
21h 55mORD-POS
5/28Tue
multi-stop
15h 19mPOS-ORD
$1,033
5/24Fri
multi-stop
21h 55mORD-POS
5/28Tue
multi-stop
26h 00mPOS-ORD
$1,114
5/24Fri
multi-stop
21h 55mORD-POS
5/27Mon
multi-stop
20h 35mPOS-ORD
$1,328
5/24Fri
multi-stop
24h 41mORD-POS
5/27Mon
multi-stop
11h 04mPOS-ORD
$1,368
5/24Fri
multi-stop
35h 20mORD-POS
5/27Mon
multi-stop
20h 35mPOS-ORD
$1,413

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Chicago - Trinidad Flights

Departure:

Chicago (ORD)United States

Return flight deals:

Trinidad - Chicago

Cabin classes:

$172
$277
$277
$38