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POS - ORD

$305 Find cheap flights from Port of Spain to Chicago O'Hare Intl Airport

This is the cheapest one-way 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 5/1. 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
Sat 5/25
Sat 6/1

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 44,979,812 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
4:05 am - 8:55 amPOS-ORD
29h 50m2 stops
9:15 pm - 6:55 pmORD-POS
20h 40m1 stop
Thu, May 9 - Tue, May 14
10:10 am - 11:29 pmPOS-ORD
14h 19m1 stop
9:15 pm - 6:55 pmORD-POS
20h 40m1 stop
Thu, May 9 - Tue, May 14
10:10 am - 11:29 pmPOS-ORD
14h 19m1 stop
9:25 pm - 1:42 amORD-POS
27h 17m3 stops
Thu, May 9 - Tue, May 14
10:10 am - 6:17 pmPOS-ORD
33h 07m3 stops
9:15 pm - 1:42 amORD-POS
27h 27m2 stops
Thu, May 9 - Tue, May 14
12:30 am - 10:59 pmPOS-ORD
23h 29m1 stop
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
$683Lufthansa
Find Deal
Thu, Jun 20 - Sun, Jun 30
12:30 am - 12:51 pmPOS-ORD
13h 21m1 stop
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
$712United Airlines
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Wed, May 8 - Tue, May 14
7:00 am - 9:44 pmPOS-ORD
15h 44m2 stops
9:55 am - 9:34 pmORD-POS
10h 39m2 stops
$715American Airlines
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Thu, May 9 - Tue, May 14
3:20 pm - 10:34 pmPOS-ORD
32h 14m2 stops
6:25 pm - 10:01 pmORD-POS
26h 36m2 stops
$789American Airlines
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Fri, Jun 21 - Sun, Jun 30
3:20 pm - 12:15 pmPOS-ORD
21h 55m2 stops
5:00 am - 10:01 pmORD-POS
16h 01m2 stops
$992British Airways
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Fri, Jun 21 - Sun, Jun 30
12:30 am - 5:08 pmPOS-ORD
17h 38m1 stop
9:15 pm - 11:23 pmORD-POS
25h 08m1 stop
$1,775United Airlines
Find Deal
Thu, Jun 20 - Sun, Jun 30

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 Sunday, 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 January, where tickets cost $566 on average. On the other hand, the most expensive months are April and July, where the average cost of tickets is $1,002 and $996 respectively.

Good to know

Low season

August

High season

June

Cheapest flight

$305
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

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 $305 for a one-way ticket and $471 for a round-trip.

  • 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 oneworld 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 $746 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 11255 reviews
7.1entertainment
6.7food
7.2comfort
7.7boarding
8.1crew
Airline reviews

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

2.0 MediocreMichelle, Apr 2024ELP - ORD
Read more about United Airlines reviews

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!

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

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

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from Port of Spain to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Port of Spain to Chicago found on KAYAK in the last 72 hours.
5/1Wed
1 stop
10h 50mPOS-ORD
$305
5/1Wed
3 stops
29h 29mPOS-ORD
$327
5/1Wed
2 stops
30h 13mPOS-ORD
$336
4/30Tue
1 stopUnited Airlines
17h 40mPOS-ORD
$437
4/30Tue
2 stopsUnited Airlines
24h 00mPOS-ORD
$2,495

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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: