POS - ORD

$348 Find Cheap Flights from Port of Spain 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 from Port of Spain to Chicago departing on 8/9. 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.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
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
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$597
Typical prices: $873-$741
Multiple Airlines
Mon 7/27Mon 8/3
POS - ORD • 1 stop
Cheapest one-way
$348
Air Canada
Sun 8/9
POS - ORD • 1 stop
Top airlines
Cheapest • from $630 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Port of Spain and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $743 (round-trip)
Shortest trip • 10h 46m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Port of Spain to Chicago

Mon, Jul 27 - Mon, Aug 3
Multiple Airlines Logo
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
$597Multiple Airlines
Fri, Jul 10 - Sat, Aug 29
Air Canada Logo
1:25 am - 2:55 pm
POS
-
ORD
14h 30m
1 stop
Air Canada Logo
6:21 pm - 12:15 am
ORD
-
POS
28h 54m
2 stops
$630Air Canada
Wed, Jul 8 - Sat, Aug 29
Air Canada Logo
1:25 am - 11:20 am
POS
-
ORD
34h 55m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$633Air Canada
Wed, Jul 8 - Fri, Aug 28
Air Canada Logo
1:25 am - 11:20 am
POS
-
ORD
34h 55m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$636Air Canada
Mon, Jul 27 - Mon, Aug 3
Multiple Airlines Logo
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
Multiple Airlines Logo
1:50 pm - 6:55 pm
ORD
-
POS
28h 05m
2 stops
$638Multiple Airlines
Wed, Jul 8 - Sat, Aug 29
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$657Air Canada
Wed, Jul 15 - Tue, Jul 21
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
3:50 pm - 12:15 am
ORD
-
POS
31h 25m
1 stop
$659Air Canada
Fri, Jul 3 - Thu, Jul 9
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
2:08 pm - 12:15 am
ORD
-
POS
33h 07m
2 stops
$663Air Canada
Wed, Jul 8 - Wed, Jul 22
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
$676Air Canada
Wed, Jul 8 - Wed, Jul 22
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$679Air Canada
Booking Insights

KAYAK's insights & trends for Port of Spain to Chicago flights

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 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 round-trip 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 $0 (return) on average. On the other hand, the most expensive months are August and July, where the average cost of round-trip tickets is $829 and $826 respectively.

Good to know

Low seasonDecember
Cheapest flight$348
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly with an average 9% 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 5 days, the lowest price for a flight from Port of Spain to Chicago O'Hare Intl Airport was $348 for a one-way ticket and $597 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 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 $720 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 $799 and an overall rating of 7.1.

  • 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.

Reviews of the 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 9842 reviews
7.3Comfort
7.1Entertainment
6.6Food
8.1Crew
7.7Boarding
Airline reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

2.0 MediocreLynn, Jun 2026
DCA - ORD
Read more United Airlines reviews

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

Awful customer service, horrible experience. We travel a lot domestic & international- worst flights to/from ever. Brief bkgd as Inhate to relive this experience: booked and chose 2 seats 4 months prior in Premium Economy - last row end seats close to bathroom, no one behind us, plenty of legroom;, underwear storage — flown this was on other airlines, love it. We receive notice 4 days before scheduled overseas flight - plane has changed, new seats assigned. Seats are split into single seats, opposites of the plane, FRONT Row so no reachable storage. Called BOTH British Air & America. American “switched planes and the seats you want are taken;” British Air “Yes, we’ll be glad to accommodate you (type type type). Just ask at the Gate and someone will give you new boarding passes with seats together in middle, OK?” — OK. —At Gate the attendant looks us up saying “No, it is an overbooked flight and yours are the only seats available.” But but but wait, “We were TOLD our seats had been switched and seated together?” Gate attendant “Well they were wrong and don’t change your seats. Your original seats are where you’ll sit.”. Right. No help WHATSOEVER. We sit opposite on way there, wife VERY disgruntled, a Tol 5 worst ways to start a 3-week bus tour of UK. We promise to NEVER FLY AMERICAN OR BROTISH AIR EVER, and we have 3 more extensive trips planned..

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Everything you need to know for your flight from Port of Spain to Chicago

Information on your arrival and departure airports