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Cheap flights from Chicago to Port of Spain from $188

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 to Port of Spain departing on 1/30. 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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0 bags

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Find the cheapest flights from Chicago to Port of Spain

Cheap round-trip flights

Air Canada Logo
2:00 pm - 1:10 amORD-POS
9h 10m1 stop
Air Canada Logo
2:15 am - 3:10 pmPOS-ORD
14h 55m1 stop
$423Air Canada
Find Deal
Fri, Nov 21 - Fri, Nov 28
Air Canada Logo
2:00 pm - 1:10 amORD-POS
9h 10m1 stop
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
18h 40m2 stops
$428Air Canada
Find Deal
Fri, Nov 21 - Fri, Nov 28
Air Canada Logo
2:00 pm - 1:10 amORD-POS
9h 10m1 stop
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
42h 40m2 stops
$433Air Canada
Find Deal
Fri, Jan 30 - Thu, Feb 5
Multiple Airlines Logo
7:43 pm - 8:00 pmORD-POS
23h 17m1 stop
Multiple Airlines Logo
2:40 pm - 9:22 amPOS-ORD
19h 42m2 stops
$452Multiple Airlines
Find Deal
Wed, Oct 8 - Wed, Oct 15
Multiple Airlines Logo
7:43 pm - 8:00 pmORD-POS
23h 17m1 stop
Multiple Airlines Logo
3:51 am - 11:45 pmPOS-ORD
20h 54m2 stops
$463Multiple Airlines
Find Deal
Wed, Oct 8 - Tue, Oct 14
Copa Airlines Logo
7:59 am - 1:46 amORD-POS
16h 47m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$532Copa Airlines
Find Deal
Wed, Oct 8 - Fri, Oct 10
United Airlines Logo
10:35 am - 11:23 pmORD-POS
11h 48m1 stop
United Airlines Logo
12:30 am - 10:02 amPOS-ORD
10h 32m1 stop
$548United Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
Copa Airlines Logo
3:22 pm - 1:46 amORD-POS
9h 24m1 stop
Copa Airlines Logo
3:46 am - 1:31 pmPOS-ORD
10h 45m1 stop
$549Copa Airlines
Find Deal
Sun, Mar 15 - Sat, Mar 21
American Airlines Logo
8:11 am - 9:20 pmORD-POS
12h 09m2 stops
American Airlines Logo
7:00 am - 10:31 pmPOS-ORD
16h 31m1 stop
$553American Airlines
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Wed, Oct 8 - Sat, Oct 11
American Airlines Logo
5:50 pm - 1:51 pmORD-POS
19h 01m1 stop
American Airlines Logo
3:34 pm - 12:00 pmPOS-ORD
21h 26m1 stop
$560American Airlines
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Thu, Mar 12 - Thu, Mar 19

Copa Airlines flights from Chicago to Port of Spain

Our best Copa Airlines deals on Chicago to Port of Spain flight tickets
Copa Airlines
Oct 8
ORD7:59 amChicago O'Hare Intl
16h 47m
1 stop
POS1:46 amPort of Spain Piarco Intl
Oct 10
POS3:51 amPort of Spain Piarco Intl
10h 50m
1 stop
ORD1:41 pmChicago O'Hare Intl
$532
Find similar
Copa Airlines
Mar 15
ORD3:22 pmChicago O'Hare Intl
9h 24m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 21
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD1:31 pmChicago O'Hare Intl
$549
Find similar
Copa Airlines
Mar 15
ORD3:22 pmChicago O'Hare Intl
9h 24m
1 stop
POS1:46 amPort of Spain Piarco Intl
Mar 20
POS3:46 amPort of Spain Piarco Intl
10h 45m
1 stop
ORD1:31 pmChicago O'Hare Intl
$552
Find similar

United Airlines flights from Chicago to Port of Spain

Our best United Airlines deals on Chicago to Port of Spain flight tickets
United Airlines
Oct 22
ORD10:35 amChicago O'Hare Intl
11h 48m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Oct 25
POS12:30 amPort of Spain Piarco Intl
10h 32m
1 stop
ORD10:02 amChicago O'Hare Intl
$548
Find similar
United Airlines
Sep 20
ORD6:00 amChicago O'Hare Intl
16h 23m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Sep 25
POS12:30 amPort of Spain Piarco Intl
10h 40m
1 stop
ORD10:10 amChicago O'Hare Intl
$549
Find similar
United Airlines
Sep 23
ORD12:45 pmChicago O'Hare Intl
9h 38m
1 stop
POS11:23 pmPort of Spain Piarco Intl
Sep 27
POS12:30 amPort of Spain Piarco Intl
10h 40m
1 stop
ORD10:10 amChicago O'Hare Intl
$659
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 September 17, 2025.
Use the filters below to find and compare flights from Chicago 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

Fri 11/21

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 11/21

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-6:55 pm

2 stops18h 40m

$428

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 1/30

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Thu 2/5

2:15 am-6:55 pm

2 stops42h 40m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/8

7:43 pm-8:00 pm

1 stop23h 17m

Port of Spain Piarco Intl

Wed 10/15

2:40 pm-9:22 am

2 stops19h 42m

$452

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/8

7:43 pm-8:00 pm

1 stop23h 17m

Port of Spain Piarco Intl

Tue 10/14

3:51 am-11:45 pm

2 stops20h 54m

$463

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/8

7:59 am-1:46 am

1 stop16h 47m

Port of Spain Piarco Intl

Fri 10/10

3:51 am-1:41 pm

1 stop10h 50m

$532

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

10:35 am-11:23 pm

1 stop11h 48m

Port of Spain Piarco Intl

Sat 10/25

12:30 am-10:02 am

1 stop10h 32m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Sat 3/21

3:46 am-1:31 pm

1 stop10h 45m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/8

8:11 am-9:20 pm

2 stops12h 09m

Port of Spain Piarco Intl

Sat 10/11

7:00 am-10:31 pm

1 stop16h 31m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

5:50 pm-1:51 pm

1 stop19h 01m

Port of Spain Piarco Intl

Thu 3/19

3:34 pm-12:00 pm

1 stop21h 26m

$560

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 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 day to depart on your flight to Port of Spain?

The cheapest day to depart from Chicago to Port of Spain is on a Sunday when prices can be found for as low as $569. Flights from Chicago 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 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 to Port of Spain

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago 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 to Port of Spain (CHI to POS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Port of Spain

Direct flights

None
There are no direct flights from Chicago to Port of Spain. There are no popular flight routes from Chicago to Port of Spain.
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  • How far is Chicago to Port of Spain Piarco Intl by plane?

    Port of Spain Piarco Intl is 2671.5 mi away from Chicago. 9h 10m is a normal flight duration for this route.

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

    Prices for flights from Chicago to Port of Spain Piarco Intl Airport refresh daily.

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

  • How old do you have to be to fly from Chicago 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 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 required for your trip to Port of Spain Piarco Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Port of Spain Piarco Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Chicago to Port of Spain?

Best airlines flying from Chicago to Port of Spain

Compare and see reviews for airlines that fly from Chicago to Port of Spain with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $480Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
American AirlinesPriceFrom $487Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Air CanadaPriceFrom $516Free CancellationRating
7.1
10,000 reviews
Search Air Canada 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?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Port of Spain. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Chicago to Port of Spain with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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?

If you are simply researching potential flights to Port of Spain, momondo offers a useful price alert feature which will track prices for flights to Port of Spain from Chicago and alert you when they change.

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