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Cheap flights from Chicago O'Hare Intl Airport to Port of Spain from $251

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 12/24. 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.
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
12h 45m1 stop
Multiple Airlines Logo
10:10 am - 9:03 pm
POS
-
ORD
12h 53m1 stop
$391Multiple Airlines
Thu, Jan 15 - Thu, Jan 22
Multiple Airlines Logo
7:20 am - 8:00 pm
ORD
-
POS
10h 40m1 stop
Multiple Airlines Logo
10:10 am - 7:38 pm
POS
-
ORD
11h 28m1 stop
$435Multiple Airlines
Fri, Jan 30 - Fri, Feb 6
Multiple Airlines Logo
10:00 am - 1:20 am
ORD
-
POS
13h 20m1 stop
Multiple Airlines Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$437Multiple Airlines
Thu, Jan 15 - Thu, Jan 22
JetBlue Logo
7:45 am - 7:11 pm
ORD
-
POS
33h 26m2 stops
JetBlue Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$443JetBlue
Thu, Jan 15 - Thu, Jan 22
Multiple Airlines Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
Multiple Airlines Logo
8:30 am - 5:44 pm
POS
-
ORD
35h 14m2 stops
$446Multiple Airlines
Fri, Jan 30 - Fri, Feb 6
Multiple Airlines Logo
8:45 pm - 1:20 am
ORD
-
POS
26h 35m1 stop
Multiple Airlines Logo
8:30 am - 5:44 pm
POS
-
ORD
35h 14m2 stops
$448Multiple Airlines
Sat, Jan 31 - Sat, Feb 7
Air Canada Logo
8:45 pm - 1:20 am
ORD
-
POS
26h 35m1 stop
Air Canada Logo
2:20 am - 1:01 pm
POS
-
ORD
12h 41m1 stop
$453Air Canada
Sat, Jan 31 - Fri, Feb 6
Air Canada Logo
10:00 am - 12:20 am
ORD
-
POS
13h 20m1 stop
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m2 stops
$473Air Canada
Thu, Mar 12 - Tue, Mar 17
Multiple Airlines Logo
6:20 pm - 12:20 am
ORD
-
POS
29h 00m2 stops
Multiple Airlines Logo
3:40 pm - 9:10 am
POS
-
ORD
18h 30m2 stops
$475Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
Air Canada Logo
7:15 am - 12:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m2 stops
$477Air Canada
Fri, Mar 13 - Tue, Mar 17

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
Jan 31
ORD8:45 pmChicago O'Hare Intl
26h 35m
1 stop
POS1:20 amPort of Spain Piarco Intl
Feb 6
POS2:20 amPort of Spain Piarco Intl
12h 41m
1 stop
ORD1:01 pmChicago O'Hare Intl
$453
Find similar
Air Canada
Mar 12
ORD10:00 amChicago O'Hare Intl
13h 20m
1 stop
POS12:20 amPort of Spain Piarco Intl
Mar 17
POS1:20 amPort of Spain Piarco Intl
18h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$473
Find similar
Air Canada
Mar 13
ORD7:15 amChicago O'Hare Intl
16h 05m
2 stops
POS12:20 amPort of Spain Piarco Intl
Mar 17
POS1:20 amPort of Spain Piarco Intl
18h 32m
2 stops
ORD6:52 pmChicago O'Hare Intl
$477
Find similar

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

Our best United Airlines deals on Chicago O'Hare Intl Airport to Port of Spain flight tickets
United Airlines
Mar 30
ORD8:53 amChicago O'Hare Intl
13h 30m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Apr 5
POS12:30 amPort of Spain Piarco Intl
20h 27m
1 stop
ORD7:57 pmChicago O'Hare Intl
$559
Find similar
United Airlines
Mar 15
ORD5:40 amChicago O'Hare Intl
16h 43m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Mar 21
POS12:30 amPort of Spain Piarco Intl
10h 37m
1 stop
ORD10:07 amChicago O'Hare Intl
$579
Find similar
United Airlines
Mar 30
ORD12:45 pmChicago O'Hare Intl
9h 38m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Apr 5
POS12:30 amPort of Spain Piarco Intl
20h 27m
1 stop
ORD7:57 pmChicago O'Hare Intl
$669
Find similar

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 December 18, 2025.
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

Thu 1/15

5:15 am-8:00 pm

1 stop12h 45m

Port of Spain Piarco Intl

Thu 1/22

10:10 am-9:03 pm

1 stop12h 53m

$391

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/30

7:20 am-8:00 pm

1 stop10h 40m

Port of Spain Piarco Intl

Fri 2/6

10:10 am-7:38 pm

1 stop11h 28m

$435

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/15

10:00 am-1:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Thu 1/22

8:20 am-5:43 pm

2 stops35h 23m

$437

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 1/15

7:45 am-7:11 pm

2 stops33h 26m

Port of Spain Piarco Intl

Thu 1/22

8:20 am-5:43 pm

2 stops35h 23m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/30

7:15 am-1:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Fri 2/6

8:30 am-5:44 pm

2 stops35h 14m

$446

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/31

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Sat 2/7

8:30 am-5:44 pm

2 stops35h 14m

$448

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 1/31

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Fri 2/6

2:20 am-1:01 pm

1 stop12h 41m

$453

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

6:20 pm-12:20 am

2 stops29h 00m

Port of Spain Piarco Intl

Mon 4/6

3:40 pm-9:10 am

2 stops18h 30m

$475

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$477

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 typical price of a round-trip flight between Chicago O'Hare Intl Airport and Port of Spain?

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.

What is the cheapest day to depart on your flight to Port of Spain?

The cheapest day to depart from Chicago O'Hare Intl Airport to Port of Spain is on a Sunday when prices can be found for as low as $569. Flights from Chicago O'Hare Intl Airport to Port of Spain on a Monday will generally be more expensive and average around $706. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Port of Spain?

In the afternoon is the cheapest time of day to fly from Chicago O'Hare Intl Airport to Port of Spain when you can find flight prices for as low as $535. Flying to Port of Spain in the afternoon is an ideal time because this is during off-peak travel hours. In the evening is when there is more demand to fly to Port of Spain, so prices are often more expensive at around $847 per ticket.

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 10m

Direct flights

None
The fastest flight from Chicago O'Hare Intl Airport to Port of Spain takes 9h 10m
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 10m 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
10,534 reviews
Search Air Canada flights
American AirlinesPriceFrom $528Free CancellationRating
7.2
11,055 reviews
Search American Airlines flights
United AirlinesPriceFrom $548Free CancellationRating
7.4
9,093 reviews
Search United 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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