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$369 Find cheap flights from Trinidad to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 7/12. 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
sáb 7/13
sáb 7/20

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Good to know

Low season

February

High season

July

Cheapest flight

$369
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 5% 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, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 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, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 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 10000 reviews
8.1Crew
7.7Boarding
7.1Entertainment
6.7Food
7.2Comfort
Airline reviews

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

4.0 OkayJames, Jun 2024RIC - ORD
Read more about United Airlines reviews

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

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.

Good with British Airways - terrible with American Airlines! Stood at gate for “mechanical problem” - plane delayed. Had to check my personal belonging with 5 empty bins available in plane, desk staff rude!!! Toilet not working- asked “to use working toilet sparingly - it may overflow in cabin!”

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

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

Book cheap flights from Trinidad to Chicago

Recent round-trip flight deals

9/22dom
1 stopUnited Airlines
20h 32mPOS-ORD
9/29dom
1 stopUnited Airlines
16h 23mORD-POS
$476
7/12sex
2 stopsFrontier
22h 53mPOS-ORD
7/16ter
2 stopsFrontier
44h 54mORD-POS
$524
9/23seg
2 stopsAmerican Airlines
23h 46mPOS-ORD
9/29dom
2 stopsAmerican Airlines
31h 59mORD-POS
$573
9/23seg
1 stopAmerican Airlines
18h 45mPOS-ORD
9/29dom
1 stopAmerican Airlines
18h 22mORD-POS
$577
6/28sex
1 stopUnited Airlines
15h 18mPOS-ORD
8/10sáb
1 stopUnited Airlines
13h 38mORD-POS
$619
7/12sex
1 stopJetBlue
10h 50mPOS-ORD
7/16ter
1 stopJetBlue
14h 45mORD-POS
$670
6/29sáb
1 stop
24h 54mPOS-ORD
8/10sáb
1 stop
21h 06mORD-POS
$679
7/28dom
3 stops
19h 59mPOS-ORD
8/18dom
2 stops
24h 27mORD-POS
$698
6/29sáb
2 stopsAmerican Airlines
14h 46mPOS-ORD
8/10sáb
1 stopAmerican Airlines
18h 30mORD-POS
$711
7/28dom
1 stopJetBlue
10h 50mPOS-ORD
8/18dom
1 stopJetBlue
15h 05mORD-POS
$840

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Recent one-way flight deals

7/12sex
1 stopCopa Airlines
10h 52mPOS-ORD
$369
7/12sex
2 stops
43h 39mPOS-ORD
$424
7/12sex
3 stops
21h 48mPOS-ORD
$475
7/11qui
1 stopUnited Airlines
24h 38mPOS-ORD
$502
7/11qui
1 stopUnited Airlines
24h 38mPOS-ORD
$810
7/11qui
2 stopsUnited Airlines
32h 25mPOS-ORD
$2,498

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Flights to Chicago

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Trinidad

Cabin classes:

$397
$232
$231
$58