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POS - ORD

$346 Find cheap flights from Port of Spain to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Port of Spain to Chicago departing on 8/2. 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

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Port of Spain to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Port of Spain to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,830,901 times on KAYAK, and here is why:

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Cheap flight deals from Port of Spain to Chicago (POS-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Port of Spain to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:14 pm - 1:11 pmPOS-ORD
22h 57m2 stops
7:00 am - 2:02 pmORD-POS
30h 02m2 stops
$346Frontier
Find Deal
Fri, Aug 2 - Thu, Aug 8
3:14 pm - 9:08 amPOS-ORD
18h 54m2 stops
5:56 pm - 2:02 pmORD-POS
19h 06m2 stops
$385Frontier
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Fri, Sep 20 - Wed, Sep 25
12:30 am - 7:57 pmPOS-ORD
20h 27m1 stop
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
$464United Airlines
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Thu, Oct 24 - Tue, Oct 29
2:22 pm - 12:15 amPOS-ORD
10h 53m1 stop
3:10 pm - 1:43 amORD-POS
9h 33m1 stop
$471Copa Airlines
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Fri, Sep 20 - Wed, Sep 25
7:58 am - 5:45 pmPOS-ORD
10h 47m1 stop
8:20 am - 9:19 pmORD-POS
11h 59m1 stop
$483American Airlines
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Tue, Sep 24 - Sun, Sep 29
3:18 pm - 11:34 pmPOS-ORD
9h 16m1 stop
8:20 am - 9:19 pmORD-POS
11h 59m2 stops
$488American Airlines
Find Deal
Fri, Sep 20 - Wed, Sep 25
4:05 am - 10:01 amPOS-ORD
30h 56m2 stops
9:24 am - 6:55 pmORD-POS
8h 31m1 stop
Wed, Jun 5 - Sun, Jun 9
2:22 pm - 12:15 amPOS-ORD
10h 53m1 stop
2:10 pm - 1:43 amORD-POS
9h 33m1 stop
$539Copa Airlines
Find Deal
Wed, Oct 23 - Sun, Nov 3
12:30 am - 7:48 amPOS-ORD
32h 18m1 stop
9:15 pm - 11:23 pmORD-POS
25h 08m1 stop
$671United Airlines
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Thu, Aug 1 - Thu, Aug 8
10:35 am - 5:35 pmPOS-ORD
32h 00m3 stops
8:25 pm - 1:42 amORD-POS
28h 17m3 stops
Wed, Jun 5 - Sun, Jun 9

Flights from Port of Spain to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Port of Spain to Chicago to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Port of Spain to Chicago?

The average price of all flights from Port of Spain to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Port of Spain to Chicago, look for departures on Wednesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Chicago, Sunday is the cheapest day to fly and Saturday is the most expensive.

What is the cheapest month to fly from Port of Spain to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Port of Spain to Chicago O'Hare Intl Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Port of Spain to Chicago O'Hare Intl Airport is April, where tickets cost $525 on average. On the other hand, the most expensive months are June and January, where the average cost of tickets is $819 and $810 respectively.

Good to know

Low season

November

High season

December

Cheapest flight

$346
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Port of Spain to Chicago

When to book flights from Port of Spain to Chicago

Are your dates flexible? Find out the best times to travel from Port of Spain to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Port of Spain to Chicago flights

  • What is the cheapest flight from Port of Spain to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Port of Spain to Chicago O'Hare Intl Airport was $346 for a round-trip ticket.

  • Do I need a passport to fly between Port of Spain and Chicago?

    A passport is required to fly from Port of Spain to Chicago.

  • Which aircraft models fly most regularly from Port of Spain to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Port of Spain to Chicago?

    Star Alliance, and oneworld are the airline alliances operating flights between Port of Spain and Chicago, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Port of Spain to Chicago, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Port of Spain to Chicago are United Airlines and American Airlines. With an average price for the route of $655 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $636 and an overall rating of 7.3.

  • How does KAYAK find such low prices on flights from Port of Spain 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 Port of Spain to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Port of Spain 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 Port of Spain 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 Port of Spain with another airline. Booking your flights between Port of Spain and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Port of Spain 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 Port of Spain up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airlines flying from Port of Spain to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Port of Spain to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Port of Spain 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 11090 reviews
7.2Comfort
6.7Food
7.1Entertainment
8.1Crew
7.7Boarding
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 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

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.

Last minute flights from Port of Spain to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Port of Spain to Chicago that are departing in the next 10 days.
5/11Sat
multi-stopUnited Airlines
17h 40mPOS-ORD
8/15Thu
multi-stopUnited Airlines
14h 58mORD-POS
$661
5/11Sat
multi-stop
24h 45mPOS-ORD
5/15Wed
multi-stop
24h 20mORD-POS
$690
5/11Sat
multi-stop
24h 45mPOS-ORD
5/15Wed
multi-stop
19h 42mORD-POS
$693
5/11Sat
multi-stop
16h 22mPOS-ORD
5/15Wed
multi-stop
27h 27mORD-POS
$782
5/10Fri
multi-stopUnited Airlines
11h 18mPOS-ORD
5/15Wed
multi-stopUnited Airlines
14h 53mORD-POS
$870
5/11Sat
multi-stop
16h 22mPOS-ORD
5/15Wed
multi-stop
17h 34mORD-POS
$900
5/10Fri
multi-stop
20h 04mPOS-ORD
5/15Wed
multi-stop
20h 40mORD-POS
$1,794

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Port of Spain - Chicago Flights

Departure:

Port of Spain (POS)Trinidad and Tobago

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Port of Spain

Cabin classes: