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Cheap flights from Chicago O'Hare Intl Airport to Port of Spain from $239

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 8/12. 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

Logo
10:27 am - 1:46 amORD-POS
38h 19m2 stops
Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
$457
Find Deal
Tue, Sep 9 - Sun, Sep 14
Logo
10:27 am - 6:55 pmORD-POS
31h 28m1 stop
Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
$462
Find Deal
Tue, Sep 16 - Fri, Sep 26
Logo
10:27 am - 4:15 amORD-POS
16h 48m1 stop
Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
$466
Find Deal
Thu, Sep 18 - Thu, Sep 25
Logo
5:05 am - 8:00 pmORD-POS
13h 55m1 stop
Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
$470
Find Deal
Thu, Sep 11 - Sat, Sep 13
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$526Copa Airlines
Find Deal
Fri, Sep 19 - Sun, Sep 28
JetBlue Logo
6:45 am - 2:34 pmORD-POS
30h 49m1 stop
JetBlue Logo
3:59 pm - 6:23 pmPOS-ORD
27h 24m1 stop
$527JetBlue
Find Deal
Tue, Sep 16 - Fri, Sep 26
Copa Airlines Logo
8:02 am - 1:46 amORD-POS
16h 44m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$541Copa Airlines
Find Deal
Tue, Sep 16 - Thu, Sep 25
United Airlines Logo
10:35 am - 11:23 pmORD-POS
11h 48m1 stop
United Airlines Logo
12:30 am - 11:05 amPOS-ORD
11h 35m1 stop
$548United Airlines
Find Deal
Tue, Sep 16 - Fri, Sep 26
American Airlines Logo
7:15 pm - 2:16 pmORD-POS
18h 01m1 stop
American Airlines Logo
3:25 pm - 8:43 amPOS-ORD
18h 18m2 stops
$553American Airlines
Find Deal
Tue, Sep 16 - Sat, Sep 27
American Airlines Logo
6:06 am - 9:36 pmORD-POS
14h 30m2 stops
American Airlines Logo
7:00 am - 7:26 pmPOS-ORD
13h 26m2 stops
$558American Airlines
Find Deal
Tue, Aug 19 - Sun, Aug 31

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
Sep 19
ORD3:07 pmChicago O'Hare Intl
9h 39m
1 stop
POS1:46 amPort of Spain Piarco Intl
Sep 28
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$526
Find similar
Copa Airlines
Sep 16
ORD8:02 amChicago O'Hare Intl
16h 44m
1 stop
POS1:46 amPort of Spain Piarco Intl
Sep 25
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$541
Find similar
Copa Airlines
Oct 22
ORD7:53 amChicago O'Hare Intl
16h 53m
1 stop
POS1:46 amPort of Spain Piarco Intl
Oct 25
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$564
Find similar

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
Sep 19
ORD10:40 amChicago O'Hare Intl
13h 40m
2 stops
POS1:20 amPort of Spain Piarco Intl
Sep 28
POS2:25 amPort of Spain Piarco Intl
11h 49m
1 stop
ORD1:14 pmChicago O'Hare Intl
$537
Find similar
Air Canada
Sep 19
ORD10:40 amChicago O'Hare Intl
13h 40m
2 stops
POS1:20 amPort of Spain Piarco Intl
Sep 28
POS2:25 amPort of Spain Piarco Intl
17h 29m
2 stops
ORD6:54 pmChicago O'Hare Intl
$542
Find similar
Air Canada
Sep 6
ORD8:25 pmChicago O'Hare Intl
27h 55m
1 stop
POS1:20 amPort of Spain Piarco Intl
Sep 19
POS2:25 amPort of Spain Piarco Intl
17h 29m
2 stops
ORD6:54 pmChicago O'Hare Intl
$547
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 August 6, 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

Tue 9/9

10:27 am-1:46 am

2 stops38h 19m

Port of Spain Piarco Intl

Sun 9/14

6:25 pm-9:18 am

1 stop15h 53m

$457

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/16

10:27 am-6:55 pm

1 stop31h 28m

Port of Spain Piarco Intl

Fri 9/26

9:10 am-9:18 am

1 stop25h 08m

$462

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/18

10:27 am-4:15 am

1 stop16h 48m

Port of Spain Piarco Intl

Thu 9/25

6:25 pm-9:18 am

1 stop15h 53m

$466

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/11

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

Sat 9/13

9:10 am-9:18 am

1 stop25h 08m

$470

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 9/19

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

Sun 9/28

3:51 am-1:41 pm

1 stop10h 50m

$526

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/16

6:45 am-2:34 pm

1 stop30h 49m

Port of Spain Piarco Intl

Fri 9/26

3:59 pm-6:23 pm

1 stop27h 24m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/16

8:02 am-1:46 am

1 stop16h 44m

Port of Spain Piarco Intl

Thu 9/25

3:51 am-1:41 pm

1 stop10h 50m

$541

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/16

10:35 am-11:23 pm

1 stop11h 48m

Port of Spain Piarco Intl

Fri 9/26

12:30 am-11:05 am

1 stop11h 35m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 9/16

7:15 pm-2:16 pm

1 stop18h 01m

Port of Spain Piarco Intl

Sat 9/27

3:25 pm-8:43 am

2 stops18h 18m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 8/19

6:06 am-9:36 pm

2 stops14h 30m

Port of Spain Piarco Intl

Sun 8/31

7:00 am-7:26 pm

2 stops13h 26m

$558

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 January is, on average, the cheapest month to fly to Port of Spain from Chicago O'Hare Intl Airport, with most prices found around $528. If you’re not able to fly to Port of Spain in January, then June is your next best option. Flight prices from Chicago O'Hare Intl Airport to Port of Spain during June average around $548.

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

Best Price Found

$239

Fastest flight time

8h 18m

Direct flights

None

Airports in Port of Spain

1 airport
The best one-way flight to Port of Spain from Chicago O'Hare Intl Airport in the past 72 hours is $239. The best round-trip flight deal from Chicago O'Hare Intl Airport to Port of Spain found on momondo in the last 72 hours is $457.
The fastest flight from Chicago O'Hare Intl Airport to Port of Spain takes 8h 18m
There are no direct flights from Chicago O'Hare Intl Airport to Port of Spain. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Port of Spain Piarco Intl Airport.
There is 1 airport near Port of Spain: Port of Spain Piarco Intl (POS)
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  • 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
United AirlinesPriceFrom $480Free CancellationRating
7.4
8,917 reviews
Search United Airlines flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
10,000 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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