$108 Find Cheap Flights from Chicago to Trinidad and Tobago

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 and Tobago departing on 4/9. 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.
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Best Trinidad and Tobago Flight Deals from Chicago

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

Port of Spain
Port of Spain1 stop$421
Scarborough
Scarborough2 stops$3,527

Good to know

Low season

December

High season

March

Cheapest flight

$108
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly with an average 22% 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 from Chicago to Trinidad and Tobago 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 from Chicago to Trinidad and Tobago with an airline and back 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 from Chicago to Trinidad and Tobago 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

  • High season is considered to be February, March and April. The cheapest month to fly from Chicago is January.
  • Morning departure is around 7% 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.
7.6
Copa AirlinesOverall score based on 1654 reviews
7.9Boarding
6.9Entertainment
7.0Food
8.1Crew
7.5Comfort
Airline reviews

Seats are getting smaller and smaller...and as hard as a rock , mediocre entertainment

6.0 GoodAnonymous, Jan 2025GYE - PTY
Read more Copa Airlines reviews

Seats are getting smaller and smaller...and as hard as a rock , mediocre entertainment

Very good flight and crew Food was a surprise on a short flight

Biggest issue was that they only had two restrooms in the back of the aircraft. Too many people for only two restrooms. The trash was overflowing and there was paper on the floor too. Long lines in the isle to use it. Food was also a bit meh. They don’t offer snacks with drinks, so you might want to buy a snack to hold you off on a longer trip, since the meals are very small.

It was first time fling in copa airline. In general I am satisfied except bag size. I got a email from copa with 17-10-6 for carry on bag. In airport the check in show 22-14-10 . However that mistake means $100,00 in over cost.

Boarding groups were called up in Spanish only. Luckily I know some of the language. They gave out grilled cheese sandwiches and a cup of fruit. I was very disappointed. I could only eat the cup of fruit because the only other option was vanilla pudding. The entertainment system and seating were great though.

Everything was smooth and crew was very polite and friendly.

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.

it was great! Boarded on-time, reasonable leg room, pleasant staff, decent food. The only thing is we were directed to Terminal 2 when the gate was actually in Terminal 1. Smooth ride. Landed early. Got off plane easily and quickly.

Crew were all excellent. Wheel chair access for my parents was very good, although it took some time. Plane was ok but entertainment system did not work. NO WIFI on plane so could not get other things done while flying or listen to my Apple Music on my iPhone.

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

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

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

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

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..

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.

Book cheap flights from Chicago to Trinidad and Tobago

Recent round-trip flight deals

3/8Sat
1 stop
17h 55mORD-POS
3/14Fri
2 stops
18h 54mPOS-ORD
$421
3/11Tue
1 stopCopa Airlines
16h 46mORD-POS
3/17Mon
1 stopCopa Airlines
11h 03mPOS-ORD
$430
3/16Sun
1 stopUnited Airlines
17h 08mORD-POS
3/19Wed
1 stopUnited Airlines
11h 53mPOS-ORD
$538
6/1Sun
1 stopAmerican Airlines
18h 15mORD-POS
6/7Sat
1 stopAmerican Airlines
16h 53mPOS-ORD
$563
6/1Sun
1 stopAmerican Airlines
18h 15mORD-POS
6/7Sat
2 stopsAmerican Airlines
12h 43mPOS-ORD
$603
2/12Wed
1 stopUnited Airlines
16h 38mORD-POS
2/21Fri
1 stopUnited Airlines
15h 25mPOS-ORD
$618
2/28Fri
2 stopsFrontier
44h 38mORD-POS
3/5Wed
2 stopsFrontier
38h 47mPOS-ORD
$644
3/19Wed
2 stopsFrontier
30h 29mORD-POS
3/27Thu
2 stopsFrontier
15h 54mPOS-ORD
$669
6/1Sun
1 stopAir Canada
28h 10mORD-POS
6/6Fri
2 stopsAir Canada
30h 03mPOS-ORD
$799
6/1Sun
1 stopAir Canada
28h 10mORD-POS
6/6Fri
1 stopAir Canada
9h 19mPOS-ORD
$811

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Recent one-way flight deals

4/9Wed
2 stops
32h 43mORD-POS
$108
4/12Sat
2 stopsFrontier
22h 44mORD-POS
$126
4/9Wed
1 stop
25h 33mORD-POS
$178
4/8Tue
2 stops
15h 26mORD-POS
$191
4/10Thu
2 stops
33h 15mORD-POS
$207
4/8Tue
1 stop
8h 46mORD-POS
$219
1/30Thu
2 stopsAmerican Airlines
11h 29mORD-POS
$241
4/11Fri
1 stop
31h 25mORD-POS
$279
1/30Thu
1 stopUnited Airlines
9h 38mORD-POS
$286
1/30Thu
3 stopsTurkish Airlines
35h 38mORD-POS
$1,871

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Everything you need to know for your flight from Chicago to Trinidad and Tobago

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