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Find cheap flights from Trinidad to Chicago from $464

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 10/24. 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
jue. 5/30
jue. 6/6

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Good to know

Low season

August

High season

June

Cheapest flight

$464
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly with an average 2% increase in price.
Flight from Port of Spain to Chicago

FAQs for booking Trinidad to Chicago flights

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

    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 Trinidad to Chicago.

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

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

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

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

    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 Chicago from Trinidad up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Trinidad to Chicago?

Find which airlines fly direct from Trinidad to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Trinidad to Chicago O'Hare Intl

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Trinidad

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +76 more

ANA, Aer Lingus, +77 more

See more direct flights
See more direct flights

Top airlines flying from Trinidad to Chicago

 
Need help choosing which airline to fly with from Trinidad to Chicago? 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.
7.4
United AirlinesOverall score based on 11186 reviews
8.1Crew
7.2Comfort
7.7Boarding
7.1Entertainment
6.7Food
Airline reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

8.0 ExcellentAnonymous, Apr 2024YUL - ORD
Read more about United Airlines reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Book cheap flights from Trinidad to Chicago

Recent round-trip flight deals

10/24jue.
1 stopUnited Airlines
10h 37mPOS-ORD
10/29mar.
1 stopUnited Airlines
14h 38mORD-POS
$464
9/24mar.
1 stopAmerican Airlines
18h 44mPOS-ORD
9/30lun.
1 stopAmerican Airlines
13h 39mORD-POS
$490
9/24mar.
1 stopAmerican Airlines
20h 36mPOS-ORD
9/30lun.
1 stopAmerican Airlines
13h 39mORD-POS
$491
9/24mar.
2 stopsAmerican Airlines
12h 42mPOS-ORD
9/30lun.
1 stopAmerican Airlines
13h 39mORD-POS
$495
9/24mar.
2 stopsAmerican Airlines
12h 42mPOS-ORD
9/30lun.
1 stopAmerican Airlines
13h 39mORD-POS
$496
9/23lun.
1 stopUnited Airlines
23h 10mPOS-ORD
9/30lun.
1 stopUnited Airlines
16h 23mORD-POS
$557
9/24mar.
2 stopsAmerican Airlines
12h 42mPOS-ORD
9/30lun.
2 stopsAmerican Airlines
13h 39mORD-POS
$570
7/29lun.
1 stopCopa Airlines
10h 09mPOS-ORD
8/15jue.
1 stopCopa Airlines
16h 47mORD-POS
$635
10/25vie.
1 stopCopa Airlines
10h 11mPOS-ORD
10/29mar.
1 stopCopa Airlines
16h 47mORD-POS
$636
10/25vie.
2 stopsAmerican Airlines
17h 22mPOS-ORD
10/29mar.
2 stopsAmerican Airlines
28h 36mORD-POS
$664

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Last minute flights from Trinidad to Chicago

Last minute flight, train and bus deals

5/1mié.
multi-stop
10h 50mPOS-ORD
5/22mié.
multi-stop
28h 33mORD-POS
$593
5/1mié.
multi-stop
10h 50mPOS-ORD
5/22mié.
multi-stop
27h 27mORD-POS
$594
5/2jue.
multi-stop
16h 16mPOS-ORD
5/22mié.
multi-stop
27h 27mORD-POS
$625
5/2jue.
multi-stop
15h 10mPOS-ORD
5/22mié.
multi-stop
27h 27mORD-POS
$635
5/2jue.
multi-stop
30h 13mPOS-ORD
5/22mié.
multi-stop
27h 27mORD-POS
$673
5/1mié.
multi-stopLufthansa
11h 18mPOS-ORD
5/22mié.
multi-stopLufthansa
14h 53mORD-POS
$733
5/2jue.
multi-stopCopa Airlines
21h 24mPOS-ORD
5/22mié.
multi-stopCopa Airlines
14h 53mORD-POS
$765
5/5dom.
multi-stopUnited Airlines
19h 37mPOS-ORD
5/13lun.
multi-stopUnited Airlines
13h 38mORD-POS
$766
5/1mié.
multi-stopAir Montenegro
15h 12mPOS-ORD
5/22mié.
multi-stopAir Montenegro
19h 35mORD-POS
$769
5/3vie.
multi-stopCopa Airlines
21h 24mPOS-ORD
5/25sáb.
multi-stopCopa Airlines
16h 46mORD-POS
$1,100

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Flights to Chicago

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Trinidad

Cabin classes:

$274
$293
$245
$52