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Cheap flights from Chicago O'Hare Intl Airport to Port of Spain from $155

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Port of Spain departing on 2/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Port of Spain

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
8:20 pm - 12:20 am
ORD
-
POS
27h 00m
1 stop
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
$358Air Canada
Mon, Mar 30 - Sun, Apr 5
Air Canada Logo
8:20 pm - 12:20 am
ORD
-
POS
27h 00m
1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$361Air Canada
Mon, Mar 30 - Sun, Apr 5
Air Canada Logo
8:00 am - 1:20 am
ORD
-
POS
15h 20m
1 stop
Air Canada Logo
2:20 am - 8:00 am
POS
-
ORD
31h 40m
2 stops
$368Air Canada
Fri, Feb 27 - Thu, Mar 5
Air Canada Logo
6:21 pm - 12:20 am
ORD
-
POS
28h 59m
2 stops
Air Canada Logo
1:20 am - 8:00 am
POS
-
ORD
31h 40m
2 stops
$371Air Canada
Mon, Mar 30 - Sun, Apr 5
Air Canada Logo
1:55 pm - 12:20 am
ORD
-
POS
9h 25m
1 stop
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
$408Air Canada
Fri, Mar 27 - Thu, Apr 2
Air Canada Logo
1:55 pm - 12:20 am
ORD
-
POS
9h 25m
1 stop
Air Canada Logo
1:20 am - 6:53 pm
POS
-
ORD
18h 33m
2 stops
$413Air Canada
Fri, Mar 27 - Thu, Apr 2
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 3:10 pm
POS
-
ORD
14h 50m
1 stop
$418Air Canada
Mon, Mar 16 - Thu, Mar 19
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 6:45 pm
POS
-
ORD
18h 25m
2 stops
$426Air Canada
Mon, Mar 16 - Thu, Mar 19
Air Canada Logo
10:00 am - 12:20 am
ORD
-
POS
13h 20m
1 stop
Air Canada Logo
1:20 am - 1:01 pm
POS
-
ORD
12h 41m
1 stop
$428Air Canada
Sun, Mar 15 - Thu, Mar 19
Multiple Airlines Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Multiple Airlines Logo
8:45 am - 9:10 am
POS
-
ORD
25h 25m
2 stops
$433Multiple Airlines
Mon, Mar 2 - Sun, Mar 8

Air Canada flights from Chicago O'Hare Intl Airport to Port of Spain

Our best Air Canada deals on Chicago O'Hare Intl Airport to Port of Spain flight tickets
Air Canada
Mar 30
ORD8:20 pmChicago O'Hare Intl
27h 00m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 5
POS1:20 amPort of Spain Piarco Intl
12h 45m
1 stop
ORD1:05 pmChicago O'Hare Intl
$358
Air Canada
Mar 30
ORD8:20 pmChicago O'Hare Intl
27h 00m
1 stop
POS12:20 amPort of Spain Piarco Intl
Apr 5
POS1:20 amPort of Spain Piarco Intl
14h 35m
2 stops
ORD2:55 pmChicago O'Hare Intl
$361
Air Canada
Feb 27
ORD8:00 amChicago O'Hare Intl
15h 20m
1 stop
POS1:20 amPort of Spain Piarco Intl
Mar 5
POS2:20 amPort of Spain Piarco Intl
31h 40m
2 stops
ORD8:00 amChicago O'Hare Intl
$368

Copa Airlines flights from Chicago O'Hare Intl Airport to Port of Spain

Our best Copa Airlines deals on Chicago O'Hare Intl Airport to Port of Spain flight tickets
Copa Airlines
Mar 13
ORD3:22 pmChicago O'Hare Intl
9h 24m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 17
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD1:31 pmChicago O'Hare Intl
$568
Copa Airlines
Mar 13
ORD3:22 pmChicago O'Hare Intl
9h 24m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 17
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD1:31 pmChicago O'Hare Intl
$583
Copa Airlines
Feb 21
ORD7:34 amChicago O'Hare Intl
16h 10m
1 stop
POS1:44 amPort of Spain Piarco Intl
Feb 28
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD12:31 pmChicago O'Hare Intl
$1,670

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Port of Spain that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 8, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Port of Spain that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-1:05 pm

1 stop12h 45m

$358

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-2:55 pm

2 stops14h 35m

$361

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 2/27

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Thu 3/5

2:20 am-8:00 am

2 stops31h 40m

$368

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

6:21 pm-12:20 am

2 stops28h 59m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-8:00 am

2 stops31h 40m

$371

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/27

1:55 pm-12:20 am

1 stop9h 25m

Port of Spain Piarco Intl

Thu 4/2

1:20 am-1:05 pm

1 stop12h 45m

$408

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/27

1:55 pm-12:20 am

1 stop9h 25m

Port of Spain Piarco Intl

Thu 4/2

1:20 am-6:53 pm

2 stops18h 33m

$413

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/16

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Thu 3/19

1:20 am-3:10 pm

1 stop14h 50m

$418

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/16

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Thu 3/19

1:20 am-6:45 pm

2 stops18h 25m

$426

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Thu 3/19

1:20 am-1:01 pm

1 stop12h 41m

$428

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/2

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Sun 3/8

8:45 am-9:10 am

2 stops25h 25m

$433

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Port of Spain

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Port of Spain?

The month of November is, on average, the cheapest month to fly to Port of Spain from Chicago O'Hare Intl Airport, with most prices found around $443. If you’re not able to fly to Port of Spain in November, then January is your next best option. Flight prices from Chicago O'Hare Intl Airport to Port of Spain during January average around $528.

When to book flights from Chicago O'Hare Intl Airport to Port of Spain

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Port of Spain according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Port of Spain (ORD to POS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Port of Spain

Fastest flight time

9h 00m

Direct flights

None
The fastest flight from Chicago O'Hare Intl Airport to Port of Spain takes 9h 00m
There are no direct flights from Chicago O'Hare Intl Airport to Port of Spain. There are no popular flight routes from Chicago O'Hare Intl Airport to Port of Spain.
Search flight deals

  • How far is Chicago O'Hare Intl to Port of Spain Piarco Intl by plane?

    Port of Spain Piarco Intl is 2686.5 mi away from Chicago O'Hare Intl. 9h 00m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Port of Spain Piarco Intl Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Port of Spain Piarco Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Port of Spain Piarco Intl Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Port of Spain Piarco Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Port of Spain Piarco Intl Airport.

  • What documentation or ID do you need to fly to Port of Spain Piarco Intl Airport?

    The travel and health documents you'll need for your trip to Port of Spain Piarco Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Port of Spain Piarco Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago O'Hare Intl Airport to Port of Spain?

Best airlines flying from Chicago O'Hare Intl Airport to Port of Spain

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Port of Spain with momondo
Airline
Rating
Free Cancellation
Price
Air CanadaPriceFrom $432Free CancellationRating
7.1
10,697 reviews
Search Air Canada flights
United AirlinesPriceFrom $501Free CancellationRating
7.4
9,254 reviews
Search United Airlines flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,249 reviews
Search American Airlines flights

Traveling to a place near Port of Spain?

Book flights to Port of Spain if you plan to visit one of these locations
Piarco

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Port of Spain?

Finding the right flight to Port of Spain from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Port of Spain quick and easy, saving you time and money.

Can I find flights from Chicago to Port of Spain with flexible booking policies on momondo?

Yes. All flights to Port of Spain from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Port of Spain?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Port of Spain from Chicago.

I’m not ready to book a flight from Chicago to Port of Spain right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Port of Spain flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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